4-(benzyloxy)-1H-indole (4-Benzyloxyindole)

Page 1

Reaxys

PubChem

eMolecules

Reactions (318)

Substances (1)

Citations (106)

Structure

Structure/Compound Data Chemical Name: 4-benzyloxy-1H-indole Reaxys Registry Number: 183150

CAS Registry Number: 20289-26-3 Type of Substance: heterocyclic Molecular Formula: C15H13NO Linear Structure Formula: C15H13NO Molecular Weight: 223.274 InChI Key: LJFVSIDBFJPKLD-UHFFFAOYSA-N

1

Synthesize | Hide Details Find similar Chemical Names and Synonyms 4-benzyloxy-1H-indole, 4-Benzyloxyindole, 4-(benzyloxy)-1H-indole, 4-(benzyloxy)indole, 4-benzyloxy indole, 4-benzyloxy-indole, 4-Benzyloxy-indol Identification Substance Label (27) Label

Reference

1

Ametamey; Vollenweider; Patt; Bourquin; Hasler; Beer; Schubiger

Journal of Labelled Compounds and Radiopharmaceuticals, 1998 , vol. 41, # 7 p. 585 - 594 Title/Abstract Full Text View citing articles Show Details

Li, Jianxiao; Li, Chunsheng; Yang, Shaorong; An, Yanni; Wu, Wanqing; Jiang, Huanfeng

Journal of Organic Chemistry, 2016 , vol. 81, # 17 p. 7771 - 7783 Title/Abstract Full Text Show Details

PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard

Patent: WO2017/3862 A1, 2017 ; Title/Abstract Full Text Show Details

N° of preparations All Preps | All Reactions 21 prep out of 318 reactions.

Available Data

N° of ref.

Identification Physical Data (8) Spectra (18) Bioactivity (6)

106


17i

Stemper, Jérémy; Isaac, Kévin; Ghosh, Nayan; Lauwick, Hortense; Le Duc, Gaëtan; Retailleau, Pascal; Voituriez, Arnaud; Betzer, Jean-François; Marinetti, Angela

Advanced Synthesis and Catalysis, 2017 , vol. 359, # 3 p. 519 - 526 Title/Abstract Full Text Show Details

2

YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta

Patent: WO2013/150529 A2, 2013 ; Title/Abstract Full Text Show Details

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda

Patent: WO2016/144703 A1, 2016 ; Title/Abstract Full Text Show Details

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; LONERGAN, David

Patent: WO2016/144702 A1, 2016 ; Title/Abstract Full Text Show Details

6a

Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni

Tetrahedron, 2016 , vol. 72, # 18 p. 2233 - 2238 Title/Abstract Full Text View citing articles Show Details

8d

Jiang, Huanfeng; Yang, Jidan; Tang, Xiaodong; Wu, Wanqing

Journal of Organic Chemistry, 2016 , vol. 81, # 5 p. 2053 - 2061 Title/Abstract Full Text View citing articles Show Details

2c

Luo, Dongping; Wu, Ge; Yang, Hang; Liu, Miaochang; Gao, Wenxia; Huang, Xiaobo; Chen, Jiuxi; Wu, Huayue

Journal of Organic Chemistry, 2016 , vol. 81, # 11 p. 4485 - 4493 Title/Abstract Full Text View citing articles Show Details

XXI

The Second Military Medical University Of The Chinese People S Liberation Army; sheng, Chunquan; zhang, wannain; jiang, zhigan; chen, wei; dong, Guoqiang; miao, Zhenyuan; yao, jianzhong

Patent: CN103254191 B, 2016 ; Title/Abstract Full Text Show Details

1i

Yoo, Woo-Jin; Nguyen, Thanh V. Q.; Guiteras Capdevila, Montse; Kobayashi, Shu

Heterocycles, 2015 , vol. 90, # 2 p. 1196 - 1204 Title/Abstract Full Text View citing articles Show Details

1m

Cheng, Yuanzheng; Yuan, Xiangai; Ma, Jing; Yu, Shouyun

Chemistry - A European Journal, 2015 , vol. 21, # 23 p. 8355 - 8359 Title/Abstract Full Text View citing articles Show Details

5c

Yang, Jin-Hui; Lou, Qin-Xin; Chen, Yan-Xue; Tang, Kang-Kang

Synthetic Communications, 2015 , vol. 45, # 16 p. 1887 - 1892 Title/Abstract Full Text View citing articles Show Details

3b

Cheng, Guolin; Weng, Yunxiang; Yang, Xifa; Cui, Xiuling

Organic Letters, 2015 , vol. 17, # 15 p. 3790 - 3793 Title/Abstract Full Text View citing articles Show Details

1g

Liu, Bing; Ji, Shun-Jun; Su, Xiao-Ming; Wang, Shun-Yi

Synthetic Communications, 2008 , vol. 38, # 8 p. 1279 - 1290 Title/Abstract Full Text View citing articles Show Details

Zi, You; Cai, Zhong-Jian; Wang, Shun-Yi; Ji, Shun-Jun

Organic Letters, 2014 , vol. 16, # 11 p. 3094 - 3097 Title/Abstract Full Text View citing articles Show Details

5

Pouwer, Rebecca H.; Deydier, Sophie M.; Le, Phuc Van; Schwartz, Brett D.; Franken, Nicole C.; Davis, Rohan A.; Coster, Mark J.; Charman, Susan A.; Edstein, Michael D.; Skinner-Adams, Tina S.; Andrews, Katherine T.; Jenkins, Ian D.; Quinn, Ronald J.

ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 2 p. 178 - 182 Title/Abstract Full Text View citing articles Show Details

20

Jiang, Zhigan; Liu, Na; Dong, Guoqiang; Jiang, Yan; Liu, Yang; He, Xiaomeng; Huang, Yahui; He, Shipeng; Chen, Wei; Li, Zhengang; Yao, Jianzhong; Miao, Zhenyuan; Zhang, Wannian; Sheng, Chunquan

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 17 p. 4090 - 4094 Title/Abstract Full Text View citing articles Show Details

61

ALEVERE MEDICAL CORPORATION; DUNCAN, Diane; KAMERZELL, Tim; PALMER, Mark, A.

Patent: WO2014/143125 A1, 2014 ; Title/Abstract Full Text Show Details

3d

Kwon, Tae Hoon; Yoon, Ik Hwan; Shin, Ji-Sun; Lee, Young Hun; Kwon, Bong Jin; Lee, Kyung-Tae; Lee, Yong Sup

Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 9 p. 2571 - 2574 Title/Abstract Full Text View citing articles Show Details


1h

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu

Organic Letters, 2012 , vol. 14, # 20 p. 5326 - 5329,4 Title/Abstract Full Text Show Details

3

Yanovsky, Inessa; Finkin-Groner, Efrat; Zaikin, Andrey; Lerman, Lena; Shalom, Hila; Zeeli, Shani; Weill, Tehilla; Ginsburg, Isaac; Nudelman, Abraham; Weinstock, Marta

Journal of Medicinal Chemistry, 2012 , vol. 55, # 23 p. 10700 - 10715 Title/Abstract Full Text View citing articles Show Details

2h

Wang, Shun-Yi; Ji, Shun-Jun

Synthetic Communications, 2008 , vol. 38, # 3 p. 465 - 472 Title/Abstract Full Text View citing articles Show Details

4a

Kemnitzer, William; Drewe, John; Jiang, Songchun; Zhang, Hong; Crogan-Grundy, Candace; Labreque, Denis; Bubenick, Monica; Attardo, Giorgio; Denis, Real; Lamothe, Serge; Gourdeau, Henriette; Tseng, Ben; Kasibhatla, Shailaja; Sui, Xiong Cai

Journal of Medicinal Chemistry, 2008 , vol. 51, # 3 p. 417 - 423 Title/Abstract Full Text View citing articles Show Details

Label

Reference

2k

Wang, Shun-Yi; Ji, Shun-Jun

Synlett, 2007 , # 14 p. 2222 - 2226 Title/Abstract Full Text View citing articles Show Details

9a

Zhang, Xiaoyan; Urbanski, Maud; Patel, Mona; Cox, Geoffrey G.; Zeck, Roxanne E.; Bian, Haiyan; Conway, Bruce R.; Beavers, Mary Pat; Rybczynski, Philip J.; Demarest, Keith T.

Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 6 p. 1696 - 1701 Title/Abstract Full Text View citing articles Show Details

1b

Ma, Shengming; Yu, Shichao; Peng, Zhihua; Guo, Hao

Journal of Organic Chemistry, 2006 , vol. 71, # 26 p. 9865 - 9868 Title/Abstract Full Text View citing articles Show Details

8

Vedejs, Edwin; Barda, David A.

Organic Letters, 2000 , vol. 2, # 8 p. 1033 - 1035 Title/Abstract Full Text View citing articles Show Details

Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi

Tetrahedron Letters, 2006 , vol. 47, # 6 p. 969 - 972 Title/Abstract Full Text View citing articles Show Details

1d

Ma, Shengming; Yu, Shichao; Peng, Zhihua

Organic and Biomolecular Chemistry, 2005 , vol. 3, # 10 p. 1933 - 1936 Title/Abstract Full Text View citing articles Show Details

A

BANYU PHARMACEUTICAL CO., LTD.

Patent: EP1541582 A1, 2005 ; Title/Abstract Full Text Show Details

1a

Zembower, David E.; Zhang, Heping; Lineswala, Jayana P.; Kuffel, Mary J.; Aytes, Shelley A.; Ames, Matthew M.

Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 2 p. 145 - 150 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (1) Related Markush Structure (RN)

Reference

11658313

Roche Palo Alto LLC

Patent: US2003/229069 A1, 2003 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (5) Melting Point

Solvent (Melting Point)

Reference

57 - 58 °C

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details

64 - 65 °C

Lloyd, David H.; Nicholas, David E.

Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4294 - 4295 Title/Abstract Full Text View citing articles Show Details


70 - 71 °C

Kruse, Lawrence I.

Heterocycles, 1981 , vol. 16, # 7 p. 1119 - 1124 Title/Abstract Full Text Show Details

59 °C

Bridges; Williams

Biochemical Journal, 1968 , vol. 107, p. 225,228 Full Text Show Details

Julia; Pascal

Chimica Therapeutica, 1970 , vol. 5, p. 279,280, 283 Full Text Show Details

72 - 74 °C

Stoll et al.

Helvetica Chimica Acta, 1955 , vol. 38, p. 1452,1469 Full Text Show Details

toluene

Crystal Property Description (3) Colour & Other Properties

Location

Reference

colourless

Paragraph 00348

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda

Patent: WO2016/144703 A1, 2016 ; Title/Abstract Full Text Show Details

yellow

Page/Page column 43

YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta

Patent: WO2013/150529 A2, 2013 ; Title/Abstract Full Text Show Details

Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.

Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860 Title/Abstract Full Text View citing articles Show Details

light-yellow

Spectra NMR Spectroscopy (11) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Chemical shifts

1H

Coupling Nuclei

Solvents (NMR Spectroscopy) dimethylsulfoxided6

Frequency (NMR Spectroscopy) 300 MHz

Original Text (NMR Spectroscopy)

Location

‘HNMR (500 IVIHz, DMSO-d6): 11.08 (s, 1H), 7.20 —7.55 (m, 5H), 6.93—7.10 (m, 3H), 6.58 (m, 1H), 6.48 (m, 1H), 5.19 (s, 2H).

Paragraph 00363

Comment (NMR Spectroscopy)

Reference PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; LONERGAN, David

Patent: WO2016/144702 A1, 2016 ; Title/Abstract Full Text Show Details

Chemical shifts

Chemical shifts

1H

1H

dimethylsulfoxided6

chloroform-d1

500 MHz

300 MHz

1H MR (500 MHz, DMSO-i): δ 11.08 (br s, 1H), 7.49 (d, J= 7.5 Hz, 2H), 7.39 (t, J= 7.5 Hz, 2H), 7.34-7.29 (m, 1H), 7.21 (t, J = 2.6 Hz, 1H), 7.016.92 (m, 2H), 6.55 (d, J= 7.2 Hz, 1H), 6.45-6.43 (m, 1H), 5.20 (s, 2H);

Paragraph 00348

1H-NMR

Page/Page column 43

(300 MHz, CDC13) ppm δ 8.15 (bs, lH, H-

l), 7.57-7.60 (m, 2H, H-12), 7.38-7.49 (m, 3H, H13+H-14), 7.16 (t, J = 8.1 Hz, 1H, H-6), 7.09-7.02 (m, 2H, H-7+H-5), 6.81-6.78 (m, 1H, H-3), 6.67 (d, J = 8.1 Hz, 1H, H- 2), 5.30 (s, 2H, H-10);

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda

Patent: WO2016/144703 A1, 2016 ; Title/Abstract Full Text Show Details

YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta

Patent: WO2013/150529 A2, 2013 ; Title/Abstract Full Text Show Details

Chemical shifts

13C

chloroform-d1

75 MHz

13C-NMR

(75 MHz, CDC13) ppm δ 152.56, 137.64,

137.36, 128.56, 127.81 , 127.42, 122.82, 122.73, 118.94, 104.81 , 101.16, 100.02, 69.99.

Page/Page column 43

YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta

Patent: WO2013/150529 A2, 2013 ; Title/Abstract Full Text Show Details

Chemical shifts

1H

CDCl3

300 MHz

Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.

Journal of Medicinal Chemistry, 2006 , vol. 49, #


10 p. 2858 - 2860 Title/Abstract Full Text View citing articles Show Details

1H

1H

1H

13C

Chemical shifts

1H

Spin-spin coupling constants

CDCl3

300 MHz

chloroform-d1

500 MHz

chloroform-d1

126 MHz

Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.

Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860 Title/Abstract Full Text View citing articles Show Details

1H-NMR (500MHz, CDCl3, δppm): 8.12 (br.s, 1H), 7.49 (br.d, J= 7.5 Hz, 1H), 7.44 (br.t, J= 7.5 Hz, 1H), 7.37 (m, 1H), 7.14 (dd, J= 8.0, 7.8 Hz, 1H), 7.10 (m, 1H), 7.04 (d, J= 8.0 Hz, 1H), 6.77 (m, 1H), 6.64 (d, J= 7.7 Hz, 1H), 5.28 (s, 2H).

Signals given

13C-NMR (126MHz, CDCl3, δppm): 152.88,137.94,137.66,128.81, 128.05, 127.66,123.00,119.23,105.02,101.46,100.40,70.27.

Signals given

BANYU PHARMACEUTICAL CO., LTD.

Patent: EP1541582 A1, 2005 ; Title/Abstract Full Text Show Details

BANYU PHARMACEUTICAL CO., LTD.

Patent: EP1541582 A1, 2005 ; Title/Abstract Full Text Show Details

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details McCormick, Kevin D.; Kobayashi, Kazumi; Goldin, Stanley M.; Laxma Reddy; Meinwald, Jerrold

Tetrahedron, 1993 , vol. 49, # 48 p. 11155 11168 Title/Abstract Full Text View citing articles Show Details

Ishibashi; Akamatsu; Iriyama; Hanaoka; Tabata; Ikeda

Chemical and Pharmaceutical Bulletin, 1994 , vol. 42, # 2 p. 271 - 276 Title/Abstract Full Text View citing articles Show Details

CDCl3

CDCl3

1H-1H

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details McCormick, Kevin D.; Kobayashi, Kazumi; Goldin, Stanley M.; Laxma Reddy; Meinwald, Jerrold

Tetrahedron, 1993 , vol. 49, # 48 p. 11155 11168 Title/Abstract Full Text View citing articles Show Details

Julia; Pascal

Chimica Therapeutica, 1970 , vol. 5, p. 279,280, 283 Full Text Show Details

NMR

IR Spectroscopy (2) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Reference

Bands

KBr

3120 - 1050 cm**(-1)

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details

Julia; Pascal

Chimica Therapeutica, 1970 , vol. 5, p. 279,280, 283 Full Text Show Details

IR

Mass Spectrometry (2) Description (Mass Spectrometry)

Location

Reference

liquid chromatography mass spectrometry (LCMS) spectrum

Paragraph 00348

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda

Patent: WO2016/144703 A1, 2016 ;


Title/Abstract Full Text Show Details

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details

spectrum

UV/VIS Spectroscopy (2) Description (UV/VIS Spectroscopy)

Solvent (UV/VIS Spectroscopy)

Absorption Maxima (UV/VIS)

Ext./Abs. Coefficient

Reference

Absorption maxima

methanol

216 nm 266 nm 289 nm

39811 l·mol-1cm-1

7943 l·mol-1cm-1

3981 l·mol-1cm-1

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details

Julia; Pascal

Chimica Therapeutica, 1970 , vol. 5, p. 279,280, 283 Full Text Show Details

UV/VIS

Fluorescence Spectroscopy (1) Description (Fluorescence Spectroscopy)

Reference

Fluorescence

Bridges; Williams

Biochemical Journal, 1968 , vol. 107, p. 225,228 Full Text Show Details

Bioactivity Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

Schering Aktiengesellschaft

Patent: US4705856 A1, 1987 ; Title/Abstract Full Text Show Details

Schering Aktiengesellschaft

Patent: US5401854 A1, 1995 ; Title/Abstract Full Text Show Details

Neurogen Corporation

Patent: US5723462 A1, 1998 ; Title/Abstract Full Text Show Details

Neurogen Corporation

Patent: US5750702 A1, 1998 ; Title/Abstract Full Text Show Details

Bigge, Christopher Franklin; Bridges, Alexander James; Casimiro-Garcia, Agustin; Fakhoury, Stephen Alan; Lee, Helen Tsenwhei; Reed, Jessica; Schaum, Robert; Schlosser, Kevin Matthew; Sexton, Karen; Zhou, Hairong

Patent: US2003/171377 A1, 2003 ; Title/Abstract Full Text Show Details

Roche Palo Alto LLC

Patent: US2003/229069 A1, 2003 ; Title/Abstract Full Text Show Details

Hoffmann et al.

Helvetica Chimica Acta, 1959 , vol. 42, p. 1557,1563,1570 Full Text Show Details

Stoll et al.

Helvetica Chimica Acta, 1955 , vol. 38, p. 1452,1469 Full Text Show Details

Troxler et al.

Helvetica Chimica Acta, 1959 , vol. 42, p. 2073,2098 Full Text Show Details

Bridges; Williams

Biochemical Journal, 1968 , vol. 107, p. 225,228 Full Text Show Details

Marchelli et al.

Canadian Journal of Chemistry, 1969 , vol. 47, p. 4375 Full Text Show Details

Julia; Pascal

Chimica Therapeutica, 1970 , vol. 5, p. 279,280, 283 Full Text Show Details

Pindur; Witzel

Archiv der Pharmazie, 1990 , vol. 323, # 7 p. 427 - 432


Title/Abstract Full Text View citing articles Show Details

Lloyd, David H.; Nichols, David E.

Tetrahedron Letters, 1983 , vol. 24, # 42 p. 4561 - 4562 Title/Abstract Full Text View citing articles Show Details

Kawase, Masami; Sinhababu, Achintya K.; Borchardt, Ronald T.

Journal of Heterocyclic Chemistry, 1987 , vol. 24, p. 1499 - 1501 Title/Abstract Full Text Show Details

Repke; Ferguson

Journal of Heterocyclic Chemistry, 1982 , vol. 19, # 4 p. 845 - 848 Title/Abstract Full Text View citing articles Show Details

Nimtz, Manfred; Haefelinger, Guenter

Liebigs Annalen der Chemie, 1987 , p. 765 - 770 Title/Abstract Full Text Show Details

Biere; Russe; Seelen

Liebigs Annalen der Chemie, 1986 , vol. 1986, # 10 p. 1749 - 1764 Title/Abstract Full Text View citing articles Show Details

Somei; Inoue; Tokutake; et al.

Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details

Somei; Tsuchiya

Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 11 p. 3145 - 3157 Title/Abstract Full Text View citing articles Show Details

2 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

Lloyd, David H.; Nicholas, David E.

Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4294 - 4295 Title/Abstract Full Text View citing articles Show Details

Brenneisen; Borner; Peter-Oesch; Schlunegger

Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details

Somei, Masanori; Yamada, Fumio; Kunimoto, Masako; Kaneko, Chikara

Heterocycles, 1984 , vol. 22, # 4 p. 797 - 801 Title/Abstract Full Text Show Details

Neef, Guenter; Eder, Ulrich; Huth, Andreas; Rahtz, Dieter; Schmiechen, Ralph; Seidelmann, Dieter

Heterocycles, 1983 , vol. 20, # 7 p. 1295 - 1313 Title/Abstract Full Text Show Details

Kruse, Lawrence I.

Heterocycles, 1981 , vol. 16, # 7 p. 1119 - 1124 Title/Abstract Full Text Show Details

Nichols; Lloyd; Johnson; Hoffman

Journal of Medicinal Chemistry, 1988 , vol. 31, # 7 p. 1406 - 1412 Title/Abstract Full Text View citing articles Show Details

McCormick, Kevin D.; Kobayashi, Kazumi; Goldin, Stanley M.; Laxma Reddy; Meinwald, Jerrold

Tetrahedron, 1993 , vol. 49, # 48 p. 11155 - 11168 Title/Abstract Full Text View citing articles Show Details

Sheppard, George S.; Pireh, Daisy; Carrera, George M.; Bures, Mark G.; Heyman, H. Robin; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 2011 - 2032 Title/Abstract Full Text View citing articles Show Details

Ishibashi; Akamatsu; Iriyama; Hanaoka; Tabata; Ikeda

Chemical and Pharmaceutical Bulletin, 1994 , vol. 42, # 2 p. 271 - 276 Title/Abstract Full Text View citing articles Show Details

Chan, Wan K.; Huang, Fu-Chih; Morrissette, Matthew M.; Warus, James D.; Moriarty, Kevin J.; Galemmo, Robert A.; Dankulich, William D.; Poli, Gregory; Sutherland, Charles A.

Journal of Medicinal Chemistry, 1996 , vol. 39, # 19 p. 3756 - 3768 Title/Abstract Full Text View citing articles Show Details

Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi

Tetrahedron Letters, 1996 , vol. 37, # 39 p. 7099 - 7102 Title/Abstract Full Text View citing articles Show Details

Dutta; Ryan; Thomas; Singer; Compton; Martin; Razdan

Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 8 p. 1591 - 1600 Title/Abstract Full Text View citing articles Show Details

Ametamey; Vollenweider; Patt; Bourquin; Hasler; Beer; Schubiger

Journal of Labelled Compounds and Radiopharmaceuticals, 1998 , vol. 41, # 7 p. 585 - 594 Title/Abstract Full Text View citing articles Show Details

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

Zembower, David E.; Zhang, Heping; Lineswala, Jayana P.; Kuffel, Mary J.; Aytes, Shelley A.; Ames, Matthew M.

Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 2 p. 145 - 150 Title/Abstract Full Text View citing articles Show Details

Ohkubo, Mitsuru; Nishimura, Teruyuki; Honma, Teruki; Nishimura, Ikuko; Ito, Satoru; Yoshinari, Tomoko; Suda, Hiroharu Arakawa Hiroyuki; Morishima, Hajime; Nishimura, Susumu

Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 23 p. 3307 - 3312 Title/Abstract Full Text View citing articles Show Details

Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.

Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details

Vedejs, Edwin; Barda, David A.

Organic Letters, 2000 , vol. 2, # 8 p. 1033 - 1035 Title/Abstract Full Text View citing articles Show Details

Pirrung, Michael C.; Deng, Liu; Li, Zhitao; Park, Kaapjoo

Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8374 - 8388 Title/Abstract Full Text View citing articles Show Details

Pirrung, Michael C.; Liu, Yufa; Deng, Liu; Halstead, Diana K.; Li, Zhitao; May, John F.; Wedel, Michael; Austin, Darrell A.; Webster, Nicholas J. G.


Journal of the American Chemical Society, 2005 , vol. 127, # 13 p. 4609 - 4624 Title/Abstract Full Text View citing articles Show Details

3 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

Sard, Howard; Kumaran, Govindaraj; Morency, Cynthia; Roth, Bryan L.; Toth, Beth Ann; He, Ping; Shuster, Louis

Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4555 - 4559 Title/Abstract Full Text View citing articles Show Details

Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi

Tetrahedron Letters, 2006 , vol. 47, # 6 p. 969 - 972 Title/Abstract Full Text View citing articles Show Details

Zhang, Xiaoyan; Urbanski, Maud; Patel, Mona; Cox, Geoffrey G.; Zeck, Roxanne E.; Bian, Haiyan; Conway, Bruce R.; Beavers, Mary Pat; Rybczynski, Philip J.; Demarest, Keith T.

Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 6 p. 1696 - 1701 Title/Abstract Full Text View citing articles Show Details

Ma, Shengming; Yu, Shichao; Peng, Zhihua

Organic and Biomolecular Chemistry, 2005 , vol. 3, # 10 p. 1933 - 1936 Title/Abstract Full Text View citing articles Show Details

Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.

Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860 Title/Abstract Full Text View citing articles Show Details

Ma, Shengming; Yu, Shichao; Peng, Zhihua; Guo, Hao

Journal of Organic Chemistry, 2006 , vol. 71, # 26 p. 9865 - 9868 Title/Abstract Full Text View citing articles Show Details

Wang, Shun-Yi; Ji, Shun-Jun

Synlett, 2007 , # 14 p. 2222 - 2226 Title/Abstract Full Text View citing articles Show Details

An, Li-Tao; Zou, Jian-Ping; Zhang, Li-Li; Zhang, Yong

Tetrahedron Letters, 2007 , vol. 48, # 24 p. 4297 - 4300 Title/Abstract Full Text View citing articles Show Details

Wang, Shun-Yi; Ji, Shun-Jun

Synthetic Communications, 2008 , vol. 38, # 3 p. 465 - 472 Title/Abstract Full Text View citing articles Show Details

Neurogen Corporation

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Cytovia, Inc.

Patent: US2006/104998 A1, 2006 ; Title/Abstract Full Text Show Details

Liu, Bing; Ji, Shun-Jun; Su, Xiao-Ming; Wang, Shun-Yi

Synthetic Communications, 2008 , vol. 38, # 8 p. 1279 - 1290 Title/Abstract Full Text View citing articles Show Details

Kemnitzer, William; Drewe, John; Jiang, Songchun; Zhang, Hong; Crogan-Grundy, Candace; Labreque, Denis; Bubenick, Monica; Attardo, Giorgio; Denis, Real; Lamothe, Serge; Gourdeau, Henriette; Tseng, Ben; Kasibhatla, Shailaja; Sui, Xiong Cai

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Frost, Jennifer M.; Dart, Michael J.; Tietje, Karin R.; Garrison, Tiffany R.; Grayson, George K.; Daza, Anthony V.; El-Kouhen, Odile F.; Miller, Loan N.; Li, Lanlan; Yao, Betty B.; Hsieh, Gin C.; Pai, Madhavi; Zhu, Chang Z.; Chandran, Prasant; Meyer, Michael D.

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Mao, Jincheng; Hua, Qiongqiong; Guo, Jun; Shi, Daqing; Ji, Shunjun

Synlett, 2008 , # 13 p. 2011 - 2016 Title/Abstract Full Text View citing articles Show Details

Pan, Xiang-Qiang; Lei, Mao-Yi; Zou, Jian-Ping; Zhang, Wei

Tetrahedron Letters, 2009 , vol. 50, # 3 p. 347 - 349 Title/Abstract Full Text View citing articles Show Details

GLAXO GROUP LIMITED

Patent: WO2009/103710 A1, 2009 ; Title/Abstract Full Text Show Details

BANYU PHARMACEUTICAL CO., LTD.

Patent: EP1541582 A1, 2005 ; Title/Abstract Full Text Show Details

Kang, Iou-Jiun; Wang, Li-Wen; Hsu, Sheng-Ju; Lee, Chung-Chi; Lee, Yen-Chun; Wu, Yen-Shian; Hsu, Tsu-An; Yueh, Andrew; Chao, Yu-Sheng; Chern, Jyh-Haur

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 15 p. 4134 - 4138 Title/Abstract Full Text View citing articles Show Details

ABBOTT LABORATORIES; BRUNCKO, Milan; DING, Hong; DOHERTY, George, A.; ELMORE, Steven, W.; HASVOLD, Lisa; HEXAMER, Laura; KUNZER, Aaron, R.; MANTEI, Robert, A.; MCCLELLAN, William, J.; PARK, Chang, H.; PARK, Cheol-min; PETROS, Andrew, M.; SONG, Xiaohong; SOUERS, Andrew, J.; SULLIVAN, Gerard, M.; TAO, Zhi-fu; WANG, Gary, T.; WANG, Le; WANG, Xilu; WENDT, Michael, D.

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4 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

ABBOTT LABORATORIES

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An, Li-Tao; Zhang, Li-Li; Zou, Jian-Ping; Zhang, Guang-Liang


Synthetic Communications, 2010 , vol. 40, # 13 p. 1978 - 1984 Title/Abstract Full Text View citing articles Show Details

NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun

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Jiang, Ran; Wu, Xiao-Jin; Zhu, Xu; Xu, Xiao-Ping; Ji, Shun-Jun

European Journal of Organic Chemistry, 2010 , # 31 p. 5946 - 5950 Title/Abstract Full Text View citing articles Show Details

Yu, Xiaolei; Lu, Aidang; Wang, Youming; Wu, Guiping; Song, Haibin; Zhou, Zhenghong; Tang, Chuchi

European Journal of Organic Chemistry, 2011 , # 5 p. 892 - 897 Title/Abstract Full Text View citing articles Show Details

Honda, Takahiro; Nagahara, Hironori; Mogi, Hiroyuki; Ban, Masakazu; Aono, Hiroyuki

Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 6 p. 1782 - 1785 Title/Abstract Full Text View citing articles Show Details

Grant, Seth W.; Gallagher, Timothy F.; Bobko, Mark A.; Duquenne, Celine; Axten, Jeffrey M.

Tetrahedron Letters, 2011 , vol. 52, # 26 p. 3376 - 3378 Title/Abstract Full Text View citing articles Show Details

Jiang, Ran; Xu, Hai-Yan; Xu, Xiao-Ping; Chu, Xue-Qiang; Ji, Shun-Jun

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Liu, Jin; Wang, Xianxue; Guo, Han; Shi, Xiaokang; Ren, Xiaoyu; Huang, Guosheng

Tetrahedron, 2012 , vol. 68, # 5 p. 1560 - 1565 Title/Abstract Full Text View citing articles Show Details

Jiang, Xiaohua; Abgottspon, Daniela; Kleeb, Simon; Rabbani, Said; Scharenberg, Meike; Wittwer, Matthias; Haug, Martina; Schwardt, Oliver; Ernst, Beat

Journal of Medicinal Chemistry, 2012 , vol. 55, # 10 p. 4700 - 4713 Title/Abstract Full Text View citing articles Show Details

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu

Organic Letters, 2012 , vol. 14, # 20 p. 5326 - 5329,4 Title/Abstract Full Text Show Details

Wu, Zhong-Liu; Podust, Larissa M.; Guengerich, F. Peter

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Lucas, Simon; Poulsen, Mette H.; Nørager, Niels G.; Barslund, Anne F.; Bach, Tinna B.; Kristensen, Anders S.; Strømgaard, Kristian

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Li, Lan-Tao; Li, Hong-Ying; Xing, Li-Juan; Wen, Li-Juan; Wang, Peng; Wang, Bin

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Yanovsky, Inessa; Finkin-Groner, Efrat; Zaikin, Andrey; Lerman, Lena; Shalom, Hila; Zeeli, Shani; Weill, Tehilla; Ginsburg, Isaac; Nudelman, Abraham; Weinstock, Marta

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Kwon, Tae Hoon; Yoon, Ik Hwan; Shin, Ji-Sun; Lee, Young Hun; Kwon, Bong Jin; Lee, Kyung-Tae; Lee, Yong Sup

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YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCKROSIN, Marta

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Ascic, Erhad; Ohm, Ragnhild G.; Petersen, Rico; Hansen, Mette R.; Hansen, Casper L.; Madsen, Daniel; Tanner, David; Nielsen, Thomas E.

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Tang, Chen-Yu; Tao, Yuan; Wu, Xin-Yan; Sha, Feng

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5 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

Zi, You; Cai, Zhong-Jian; Wang, Shun-Yi; Ji, Shun-Jun

Organic Letters, 2014 , vol. 16, # 11 p. 3094 - 3097 Title/Abstract Full Text View citing articles Show Details

Zheng, Jing; Zhang, Yan; Cui, Sunliang

Organic Letters, 2014 , vol. 16, # 13 p. 3560 - 3563 Title/Abstract Full Text View citing articles Show Details

Jiang, Zhigan; Liu, Na; Dong, Guoqiang; Jiang, Yan; Liu, Yang; He, Xiaomeng; Huang, Yahui; He, Shipeng; Chen, Wei; Li, Zhengang; Yao, Jianzhong; Miao, Zhenyuan; Zhang, Wannian; Sheng, Chunquan

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ALEVERE MEDICAL CORPORATION; DUNCAN, Diane; KAMERZELL, Tim; PALMER, Mark, A.

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Wang, Qiang; Qi, Zisong; Xie, Fang; Li, Xingwei

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 2-3 p. 355 - 360 Title/Abstract Full Text View citing articles Show Details

Yoo, Woo-Jin; Nguyen, Thanh V. Q.; Guiteras Capdevila, Montse; Kobayashi, Shu

Heterocycles, 2015 , vol. 90, # 2 p. 1196 - 1204 Title/Abstract Full Text View citing articles Show Details

Cheng, Yuanzheng; Yuan, Xiangai; Ma, Jing; Yu, Shouyun


Chemistry - A European Journal, 2015 , vol. 21, # 23 p. 8355 - 8359 Title/Abstract Full Text View citing articles Show Details

Yang, Jin-Hui; Lou, Qin-Xin; Chen, Yan-Xue; Tang, Kang-Kang

Synthetic Communications, 2015 , vol. 45, # 16 p. 1887 - 1892 Title/Abstract Full Text View citing articles Show Details

Cheng, Guolin; Weng, Yunxiang; Yang, Xifa; Cui, Xiuling

Organic Letters, 2015 , vol. 17, # 15 p. 3790 - 3793 Title/Abstract Full Text View citing articles Show Details

Zhao, Jing; Cheng, Xiuzhi; Le, Jun; Yang, Wei; Xue, Fengtian; Zhang, Xuan; Jiang, Chao

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Zhu, Dianhu; Gu, Yang; Lu, Long; Shen, Qilong

Journal of the American Chemical Society, 2015 , vol. 137, # 33 p. 10547 - 10553 Title/Abstract Full Text View citing articles Show Details

Xu, Lanting; Zhang, Chao; He, Yupeng; Tan, Lushi; Ma, Dawei

Angewandte Chemie - International Edition, 2016 , vol. 55, # 1 p. 321 - 325 Angew. Chem., 2016 , vol. 128, # 1 p. 329 - 333,5 Title/Abstract Full Text View citing articles Show Details

Jiang, Huanfeng; Yang, Jidan; Tang, Xiaodong; Wu, Wanqing

Journal of Organic Chemistry, 2016 , vol. 81, # 5 p. 2053 - 2061 Title/Abstract Full Text View citing articles Show Details

Le, Jun; Gao, Yadong; Ding, Yousong; Jiang, Chao

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Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni

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Kim, Youyoung; Park, Juhyeon; Chang, Sukbok

Organic Letters, 2016 , vol. 18, # 8 p. 1892 - 1895 Title/Abstract Full Text View citing articles Show Details

Luo, Dongping; Wu, Ge; Yang, Hang; Liu, Miaochang; Gao, Wenxia; Huang, Xiaobo; Chen, Jiuxi; Wu, Huayue

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SRI INTERNATIONAL; JONG, Ling; CHANG, Chih-Tsung; PARK, Jaehyeon

Patent: WO2016/114816 A1, 2016 ; Title/Abstract Full Text Show Details

Tu, Daoquan; Cheng, Xiuzhi; Gao, Yadong; Yang, Panpan; Ding, Yousong; Jiang, Chao

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 31 p. 7443 - 7446 Title/Abstract Full Text View citing articles Show Details

Li, Jianxiao; Li, Chunsheng; Yang, Shaorong; An, Yanni; Wu, Wanqing; Jiang, Huanfeng

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6 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda

Patent: WO2016/144703 A1, 2016 ; Title/Abstract Full Text Show Details

PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; LONERGAN, David

Patent: WO2016/144702 A1, 2016 ; Title/Abstract Full Text Show Details

The Second Military Medical University Of The Chinese People S Liberation Army; sheng, Chunquan; zhang, wannain; jiang, zhigan; chen, wei; dong, Guoqiang; miao, Zhenyuan; yao, jianzhong

Patent: CN103254191 B, 2016 ; Title/Abstract Full Text Show Details

Nanjing University of Science & Technology; Jiang, Chao; Le, Jun

Patent: CN105622585 A, 2016 ; Title/Abstract Full Text Show Details

PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard

Patent: WO2017/3862 A1, 2017 ; Title/Abstract Full Text Show Details

Stemper, Jérémy; Isaac, Kévin; Ghosh, Nayan; Lauwick, Hortense; Le Duc, Gaëtan; Retailleau, Pascal; Voituriez, Arnaud; Betzer, Jean-François; Marinetti, Angela

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