Quaternary ammonium N,N-dichloroamines as topical, antimicrobial agents

被引：24

作者：

Francavilla, Charles ^{[1
]}

Low, Eddy ^{[1
]}

Nair, Satheesh ^{[1
]}

Kim, Bum ^{[1
]}

Shiau, Timothy P. ^{[1
]}

Debabov, Dmitri ^{[1
]}

Celeri, Chris ^{[1
]}

Alvarez, Nichole ^{[1
]}

Houchin, Ashley ^{[1
]}

Xu, Ping ^{[1
]}

Najafi, Ron ^{[1
]}

Jain, Rakesh ^{[1
]}

机构：

[1] NovaBay Pharmaceut Inc, Emeryville, CA 94608 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 10期

关键词：

N-Chloroamaines; Antimicrobial agents; Taurine; Minimum bactericidal concentration; Quaternary ammonium; N-CHLOROTAURINE; PHASE-II; TOLERABILITY; CHLORAMINE; TOLERANCE; CHEMISTRY; EFFICACY; MODEL; ACIDS;

D O I：

10.1016/j.bmcl.2009.03.120

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of backbone modified and sulfonic acid replacement analogs of our topical, clinical candidate (iii) were synthesized. Their antimicrobial activities and aqueous stabilities at pH 4 and pH 7 were determined, and has led us to identify quaternary ammonium N,N-dichloroamines as a new class of topical antimicrobial agents. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2731 / 2734

页数：4

共 28 条

[1] A combinatorial method for solution-phase synthesis of labeled bivalent β-turn mimics
Angell, Yu
Chen, Dianjun
Brahimi, Fouad
Saragovi, H. Uri
Burgess, Kevin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) : 556 - 565
[2] Protein sites of attack of N-chlorotaurine in Escherichia coli
Arnitz, R
Sarg, B
Ott, HW
Neher, A
Lindner, H
Nagl, M
[J]. PROTEOMICS, 2006, 6 (03) : 865 - 869
[3] Benzodiazepine receptor ligands.: 4.: Synthesis and pharmacological evaluation of 3-heteroaryl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides
Costanzo, A
Guerrini, G
Ciciani, G
Bruni, F
Selleri, S
Costa, B
Martini, C
Lucacchini, A
Aiello, PM
Ipponi, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (12) : 2218 - 2226
[4] Aryl 1-but-3-ynyl-4-phenyl-1,2,3,6-tetrahydropyridines as potential antipsychotic agents: Synthesis and structure-activity relationships
Glase, SA
Akunne, HC
Heffner, TG
Jaen, JC
MacKenzie, RG
Meltzer, LT
Pugsley, TA
Smith, SJ
Wise, LD
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (16) : 3179 - 3187
[5] SIMPLE PERFORMIC ACID OXIDATION OF ACETYLTHIO GROUP TO SULFONIC-ACID AND ITS APPLICATION IN SYNTHESES OF 2-SUBSTITUTED TAURINES
HIGASHIURA, K
IENAGA, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) : 764 - 766
[6] A MECHANISTIC STUDY OF THE MITSUNOBU ESTERIFICATION REACTION
HUGHES, DL
REAMER, RA
BERGAN, JJ
GRABOWSKI, EJJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) : 6487 - 6491
[7] A novel synthesis of chiral guanidinium receptors and their use in unfolding the energetics of enantiorecognition of chiral carboxylates
Jadhav, Vinod D.
Schmidtchen, Franz P.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03) : 1077 - 1087
[8] N,N-Dichloroaminosulfonic acids as novel topical antimicrobial agents
Low, Eddy
Nair, Satheesh
Shiau, Timothy
Belisle, Barbara
Debabov, Dmitri
Celeri, Chris
Zuck, Meghan
Najafi, Ron
Georgopapadakou, Nafsika
Jain, Rakesh
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (01) : 196 - 198
[9] CHEMISTRY OF NATURALLY-OCCURRING POLYAMINES .10. NONMETABOLIZABLE DERIVATIVES OF SPERMINE AND SPERMIDINE
NAGARAJAN, S
GANEM, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) : 4856 - 4861
[10] The postantibiotic effect of N-chlorotaurine on Staphylococcus aureus.: Application in the mouse peritonitis model
Nagl, M
Hengster, P
Semenitz, E
Gottardi, W
[J]. JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1999, 43 (06) : 805 - 809

← 1 2 3 →