3-(2-bromoethyl)-1H-indole by Asch

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2 substances in Reaxys

2016-06-11 19h:55m:14s (EST)

1 substances in Reaxys

2016-06-11 19h:55m:40s (EST)

1. Query NH

Search as: As drawn 2. Query

(1. Query) AND itemno in (1)

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Reaxys ID 126308 View in Reaxys

1/1 CAS Registry Number: 3389-21-7 Chemical Name: 3-(2-bromoethyl)-1H-indole; 3-(2-bromo-ethyl)-1H-indole; 3-(2-bromoethyl)-indole; 2-(3-indolyl)ethyl bromide; 3-(2-bromo-ethyl)-indole; 3-(2-bromoethyl) indole; 3-(2bromoethyl)indole Linear Structure Formula: BrCH2CH2C8H5NH Molecular Formula: C10H10BrN Molecular Weight: 224.1 Type of Substance: heterocyclic InChI Key: NTLAICDKHHQUGC-UHFFFAOYSA-N Note:

Substance Label (26) Label References 1

Courant, Thibaut; Kumarn, Sirirat; He, Long; Retailleau, Pascal; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 5; (2013); p. 836 - 840, View in Reaxys; Bertamino, Alessia; Ostacolo, Carmine; Ambrosino, Paolo; Musella, Simona; Di Sarno, Veronica; Ciaglia, Tania; Soldovieri, Maria Virginia; Iraci, Nunzio; Fernandez Carvajal, Asia; De La Torre-Martinez, Roberto; Ferrer-Montiel, Antonio; Gonzalez Muniz, Rosario; Novellino, Ettore; Taglialatela, Maurizio; Campiglia, Pietro; Gomez-Monterrey, Isabel; Journal of Medicinal Chemistry; vol. 59; nb. 5; (2016); p. 2179 - 2191, View in Reaxys

Shen, Mei-Hua; Xu, Ke; Sun, Chu-Han; Xu, Hua-Dong; Organic and Biomolecular Chemistry; vol. 14; nb. 4; (2016); p. 1272 - 1276, View in Reaxys

BEI-9

Patent; TUSKEGEE UNIVERSITY; Samuel, Temesgen; Yehualaeshet, Teshome; Serbessa, Tesfaye; Fadlalla, Khalda; US2015/164860; (2015); (A1) English, View in Reaxys

Li, Haokun; Wang, Zhonglei; Zu, Liansuo; RSC Advances; vol. 5; nb. 75; (2015); p. 60962 - 60965, View in Reaxys

Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 11978,4, View in Reaxys

Chen, Chaohuang; Ouyang, Li; Lin, Quanfu; Liu, Yanpin; Hou, Chuanqi; Yuan, Yaofeng; Weng, Zhiqiang; Chemistry - A European Journal; vol. 20; nb. 3; (2014); p. 657 - 661, View in Reaxys

Schunk, Stefan; Linz, Klaus; Hinze, Claudia; Frormann, Sven; Oberboersch, Stefan; Sundermann, Bernd; Zemolka, Saskia; Englberger, Werner; Germann, Tieno; Christoph, Thomas; Koegel, BabetteY.; Schroeder, Wolfgang; Harlfinger, Stephanie; Saunders, Derek; Kless, Achim; Schick, Hans; Sonnenschein, Helmut; ACS Medicinal Chemistry Letters; vol. 5; nb. 8; (2014); p. 857 - 862, View in Reaxys

Do, Quang T.; Nguyen, Giang T.; Celis, Victor; Phillips, Robert S.; Archives of Biochemistry and Biophysics; vol. 560; (2014); p. 20 - 26, View in Reaxys

SM 12b

Shenje, Raynold; Martin, M. Cynthia; France, Stefan; Angewandte Chemie - International Edition; vol. 53; nb. 50; (2014); p. 13907 - 13911; Angew. Chem.; vol. 126; nb. 50; (2014); p. 14127 - 14131,5, View in Reaxys

Eschenbrenner-Lux, Vincent; Dueckert, Heiko; Khedkar, Vivek; Bruss, Hanna; Waldmann, Herbert; Kumar, Kamal; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2294 - 2304, View in Reaxys

Fuentes, Lilia; Hernandez-Juarez, Mireya; Teran, Joel L.; Quintero, Leticia; Sartillo-Piscil, Fernando; Synlett; vol. 24; nb. 7; (2013); p. 878 - 882; Art.No: ST-2013-S0037-L, View in Reaxys

S10

Oisaki, Kounosuke; Abe, Junpei; Kanai, Motomu; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4569 - 4572, View in Reaxys

Lin, Qingyu; Chu, Lingling; Qing, Feng-Ling; Chinese Journal of Chemistry; vol. 31; nb. 7; (2013); p. 885 891, View in Reaxys

Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys

26t

Suzuki, Takayoshi; Ota, Yosuke; Ri, Masaki; Bando, Masashige; Gotoh, Aogu; Itoh, Yukihiro; Tsumoto, Hiroki; Tatum, Prima R.; Mizukami, Tamio; Nakagawa, Hidehiko; Iida, Shinsuke; Ueda, Ryuzo; Shirahige, Katsuhiko; Miyata, Naoki; Journal of Medicinal Chemistry; vol. 55; nb. 22; (2012); p. 9562 - 9575, View in Reaxys

Patent; MYREXIS, INC.; KUMAR, Dange Vijay; SLATTUM, Paul M.; YAGER, Kraig M.; SHENDEROVICH, Mark D.; TANGALLAPALLY, Rajendra; KIM, Se-Ho; WO2012/177782; (2012); (A1) English, View in Reaxys

122

Patent; PFIZER LIMITED; US2008/103130; (2008); (A1) English, View in Reaxys

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Flick, Andrew C.; Padwa, Albert; Tetrahedron Letters; vol. 49; nb. 40; (2008); p. 5739 - 5741, View in Reaxys

Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W.; Organic and Biomolecular Chemistry; vol. 5; nb. 1; (2007); p. 103 - 113, View in Reaxys

Wanninger, Claudia; Wagenknecht, Hans-Achim; Synlett; nb. 13; (2006); p. 2051 - 2054, View in Reaxys

Padwa, Albert; Lynch, Stephen M.; Mejia-Oneto, Jose M.; Zhang, Hongjun; Journal of Organic Chemistry; vol. 70; nb. 6; (2005); p. 2206 - 2218, View in Reaxys

Padwa, Albert; Brodney, Michael A.; Lynch, Stephen M.; Rashatasakhon, Paitoon; Wang, Qiu; Zhang, Hongjun; Journal of Organic Chemistry; vol. 69; nb. 11; (2004); p. 3735 - 3745, View in Reaxys

6 (Table 1, run 9)

Blass, Benjamin E.; Coburn, Keith R.; Faulkner, Amy L.; Seibel, William L.; Srivastava, Anil; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2153 - 2155, View in Reaxys

Lynch, Stephen M.; Bur, Scott K.; Padwa, Albert; Organic Letters; vol. 4; nb. 26; (2002); p. 4643 - 4645, View in Reaxys

33(3)

Luo; Williams; Read; Curran; Journal of Organic Chemistry; vol. 66; nb. 12; (2001); p. 4261 - 4266, View in Reaxys

Liu, Xiaodong; Verkade, John G.; Journal of Organic Chemistry; vol. 64; nb. 13; (1999); p. 4840 - 4843, View in Reaxys

Patent-Specific Data (6) References Patent; TUSKEGEE UNIVERSITY; Samuel, Temesgen; Yehualaeshet, Teshome; Serbessa, Tesfaye; Fadlalla, Khalda; US2015/164860; (2015); (A1) English, View in Reaxys Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); (A1) English, View in Reaxys Patent; DONG-A PHARM.CO., LTD.; KIM, Soon-Hoe; IM, Weon-Bin; CHOI, Sung-Hak; CHOI, Sun-Ho; SOHN, Ju-Hee; SUNG, Hyun-Jung; KIM, Mi-Yeon; CHO, Kang-Hun; SOHN, Tae-Kyoung; WO2011/132901; (2011); (A2) English, View in Reaxys Patent; INSTITUT UNIV. DE CIENCIA I TECNOLOGIA, S.A.; CASTELLS BOLIART, Josep; MIGUEL CENTENO, David Enrique; PASCUAL GILABERT, Marta; WO2010/150206; (2010); (A1) English, View in Reaxys Patent; JANSSEN PHARMACEUTICA NV; WO2009/37343; (2009); (A1) English, View in Reaxys Patent; Janssen Pharmaceutica N.V.; US6352999; (2002); (B1) English, View in Reaxys Melting Point (6) 1 of 6

Melting Point [°C]

90 - 93

Location

supporting information

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys 2 of 6

Melting Point [°C]

97 - 98

Jirkovsky,I. et al.; Journal of Heterocyclic Chemistry; vol. 12; (1975); p. 937 - 940, View in Reaxys; Eryshev et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1313; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1493, View in Reaxys 3 of 6

Melting Point [°C]

100

Najer et al.; Bulletin de la Societe Chimique de France; (1963); p. 2831,2837, View in Reaxys 4 of 6

Melting Point [°C]

98.5 - 99

Solvent (Melting Point)

diethyl ether; petroleum ether

Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86, View in Reaxys 5 of 6

Melting Point [°C]

100 - 102

Fish et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 3668,3670, View in Reaxys 6 of 6

Melting Point [°C]

98 - 99

Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26, View in Reaxys Chromatographic Data (2)

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Chromatographic data

Location

TLC (Thin layer chromatography) LC (Liquid chromatography)

Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys supporting information

Crystal Property Description (5) Colour & Other Location Properties colourless

References

supporting information

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys References Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 - 11978,4, View in Reaxys

white

Do, Quang T.; Nguyen, Giang T.; Celis, Victor; Phillips, Robert S.; Archives of Biochemistry and Biophysics; vol. 560; (2014); p. 20 - 26, View in Reaxys

yellow

Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys

white

supporting information

yellow

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W.; Organic and Biomolecular Chemistry; vol. 5; nb. 1; (2007); p. 103 - 113, View in Reaxys

NMR Spectroscopy (13) 1 of 13

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Do, Quang T.; Nguyen, Giang T.; Celis, Victor; Phillips, Robert S.; Archives of Biochemistry and Biophysics; vol. 560; (2014); p. 20 - 26, View in Reaxys

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4 of 13

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.3

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Oisaki, Kounosuke; Abe, Junpei; Kanai, Motomu; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4569 - 4572, View in Reaxys 5 of 13

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.7

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Oisaki, Kounosuke; Abe, Junpei; Kanai, Motomu; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4569 - 4572, View in Reaxys 6 of 13

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys 7 of 13

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys 8 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

5/12

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Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys 9 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys 10 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

Page/Page column 22

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3, 400MHz): δ 8.10-7.88 (bs, 1H), 7.58 (d, J =8Hz, 1H), 7.38-7.34 (m, 1H), 7.24-7.20 (m, 1H), 7.19-7.08 (m, 2H), 3.65-3.60 (m, 2H), 3.35-3.30 (m, 2H).

Patent; DONG-A PHARM.CO., LTD.; KIM, Soon-Hoe; IM, Weon-Bin; CHOI, Sung-Hak; CHOI, Sun-Ho; SOHN, Ju-Hee; SUNG, Hyun-Jung; KIM, Mi-Yeon; CHO, Kang-Hun; SOHN, Tae-Kyoung; WO2011/132901; (2011); (A2) English, View in Reaxys 11 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Yang, Jun; Song, Hao; Xiao, Xue; Wang, Jue; Qin, Yong; Organic Letters; vol. 8; nb. 10; (2006); p. 2187 - 2190, View in Reaxys; Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W.; Organic and Biomolecular Chemistry; vol. 5; nb. 1; (2007); p. 103 - 113, View in Reaxys 12 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W.; Organic and Biomolecular Chemistry; vol. 5; nb. 1; (2007); p. 103 - 113, View in Reaxys

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13 of 13

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Yang, Jun; Song, Hao; Xiao, Xue; Wang, Jue; Qin, Yong; Organic Letters; vol. 8; nb. 10; (2006); p. 2187 - 2190, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

ATR (attenuated total reflectance); Intensity of IR bands; Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W.; Organic and Biomolecular Chemistry; vol. 5; nb. 1; (2007); p. 103 - 113, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

Oisaki, Kounosuke; Abe, Junpei; Kanai, Motomu; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4569 - 4572, View in Reaxys

electrospray ionisation (ESI); spectrum

supporting information

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys

high resolution mass spectrometry (HRMS); electron impact (EI); spectrum

supporting information

Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1781 - 1790, View in Reaxys

Pharmacological Data (5) 1 of 5

Comment (Pharmacological Data)

Bioactivities present

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Location

Paragraph

Comment (Pharmacological Data)

physiological behaviour discussed

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Patent; TUSKEGEE UNIVERSITY; Samuel, Temesgen; Yehualaeshet, Teshome; Serbessa, Tesfaye; Fadlalla, Khalda; US2015/164860; (2015); (A1) English, View in Reaxys 3 of 5

Effect (Pharmacological Data)

bronchodilatoric

Species or Test-System (Pharmacological Data)

guinea-pig trachea

Sex

male and female

Concentration (Pharmacological Data)

0.01 - 1 mmol/l

Method (Pharmacological Data)

tension changes of samples recorded with isometric transducer; cumulative conc.-relaxation curve for title comp. constructed

Further Details (Pharmacological Data)

reference comp.: theophylline (pD2 = 4.69, 77.0 percent relaxation at 0.1 mmol/l); pD2: negative log of EC50

Type (Pharmacological Data)

pD2

Value of Type (Pharmacological Data)

4.70 dimensionless

Results

title comp. induced relaxation 55.9 percent at 0.1 mmol/l

Rios-Santamarina, Inmaculada; Garcia-Domenech, Ramon; Galvez, Jorge; Morcillo Esteban, Jesus; Santamaria, Pedro; Cortijo, Julio; European Journal of Pharmaceutical Sciences; vol. 22; nb. 4; (2004); p. 271 - 277, View in Reaxys 4 of 5

Comment (Pharmacological Data)

in vitro antifungal activity against Sacharomyces cerevisiae (CECT 1324) and Candida albicans (CECT 1392): MIC=2-3.2 μg/mL

Pastor; Garcia-Domenech; Galvez; Wolski; Garcia; Bioorganic and Medicinal Chemistry Letters; vol. 8; nb. 18; (1998); p. 2577 - 2582, View in Reaxys 5 of 5

Comment (Pharmacological Data)

antifouling activity

Kon-Ya, Kazumi; Shimidzu, Nobuyoshi; Miki, Wataru; Endo, Mamoru; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 12; (1994); p. 2178 - 2181, View in Reaxys

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