Literature DB >> 6247489

Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.

J H Wikel, C J Paget, D C DeLong, J D Nelson, C Y Wu, J W Paschal, A Dinner, R J Templeton, M O Chaney, N D Jones, J W Chamberlin.   

Abstract

The synthesis and antirhinovirus activity of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine (4 and 5) are reported. The structural assignments of 4 and 5 are based upon 13C NMR spectra of both isomers and also X-ray analysis of 5. The anti-isomer 5 was more potent than the syn-isomer 4 when compared as an inhibitor of rhinovirus multiplication in vitro. Both isomers inhibited multiplication of 15 different serotypes of rhinovirus.

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Year:  1980        PMID: 6247489     DOI: 10.1021/jm00178a004

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  14 in total

1.  Comparative studies on the modes of action of the antirhinovirus agents Ro 09-0410, Ro 09-0179, RMI-15,731, 4',6-dichloroflavan, and enviroxime.

Authors:  Y Ninomiya; M Aoyama; I Umeda; Y Suhara; H Ishitsuka
Journal:  Antimicrob Agents Chemother       Date:  1985-04       Impact factor: 5.191

2.  Valosin-containing protein (VCP/p97) is required for poliovirus replication and is involved in cellular protein secretion pathway in poliovirus infection.

Authors:  Minetaro Arita; Takaji Wakita; Hiroyuki Shimizu
Journal:  J Virol       Date:  2012-02-29       Impact factor: 5.103

Review 3.  Transmission and control of rhinovirus colds.

Authors:  L C Jennings; E C Dick
Journal:  Eur J Epidemiol       Date:  1987-12       Impact factor: 8.082

4.  Discovery of itraconazole with broad-spectrum in vitro antienterovirus activity that targets nonstructural protein 3A.

Authors:  Qianqian Gao; Shilin Yuan; Chao Zhang; Ying Wang; Yizhuo Wang; Guimei He; Shuyi Zhang; Ralf Altmeyer; Gang Zou
Journal:  Antimicrob Agents Chemother       Date:  2015-02-17       Impact factor: 5.191

5.  Mutations in the 2C region of poliovirus responsible for altered sensitivity to benzimidazole derivatives.

Authors:  H Shimizu; M Agoh; Y Agoh; H Yoshida; K Yoshii; T Yoneyama; A Hagiwara; T Miyamura
Journal:  J Virol       Date:  2000-05       Impact factor: 5.103

6.  3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus.

Authors:  Jinwoo Kim; Jin Soo Shin; Sunjoo Ahn; Soo Bong Han; Young-Sik Jung
Journal:  ACS Med Chem Lett       Date:  2018-04-13       Impact factor: 4.345

7.  Topical enviroxime against rhinovirus infection.

Authors:  R A Levandowski; C T Pachucki; M Rubenis; G G Jackson
Journal:  Antimicrob Agents Chemother       Date:  1982-12       Impact factor: 5.191

8.  The antiviral compound enviroxime targets the 3A coding region of rhinovirus and poliovirus.

Authors:  B A Heinz; L M Vance
Journal:  J Virol       Date:  1995-07       Impact factor: 5.103

9.  Oxysterol-binding protein family I is the target of minor enviroxime-like compounds.

Authors:  Minetaro Arita; Hirotatsu Kojima; Tetsuo Nagano; Takayoshi Okabe; Takaji Wakita; Hiroyuki Shimizu
Journal:  J Virol       Date:  2013-01-30       Impact factor: 5.103

Review 10.  Strategies to develop antivirals against enterovirus 71.

Authors:  Rei-Lin Kuo; Shin-Ru Shih
Journal:  Virol J       Date:  2013-01-22       Impact factor: 4.099

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