1-(4S-Benzyl-2-oxo-oxazolidin-3-yl)-2R-butyl-butane-1,3-dione | 235786-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-(4S-Benzyl-2-oxo-oxazolidin-3-yl)-2R-butyl-butane-1,3-dione
• 英文别名: (2R)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-butylbutane-1,3-dione
• CAS: 235786-14-8
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: IYDOEBWUVCXTSO-JKSUJKDBSA-N

物化性质

• 沸点：
  479.8±28.0 °C(predicted)
• 密度：
  1.160±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4S-Benzyl-2-oxo-oxazolidin-3-yl)-2R-butyl-butane-1,3-dione 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 双氧水 、 sodium acetate 、 sodium cyanoborohydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 BnO-N(For)bAla(2R-Bu,3-Me)-Gly(tBu)-NMe2
  参考文献：
  名称：

  Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chain

  摘要：

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00532-8
• 作为产物：
  描述：

  己酰氯 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 1-(4S-Benzyl-2-oxo-oxazolidin-3-yl)-2R-butyl-butane-1,3-dione
  参考文献：
  名称：

  Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chain

  摘要：

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00532-8

文献信息

• Antibacterial agents
  申请人：British Biotech Pharmaceuticals Ltd.

  公开号：US06423690B1

  公开（公告）日：2002-07-23

  A method for the treatment of bacterial infections in humans and non-human mammals, which comprises administering to a subject suffering such infection an antibacterially effective dose of a compound of formula (I) or a pharmaceutically or veterinarily acceptable salt thereof: wherein: R1 represents hydrogen, or C1-C6 alkyl or C1-C6 alkyl substituted by one or more halogen atoms; R2 represents a group R10—(X)n—(ALK)m— wherein R10 represents hydrogen, or a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl, aryl, or heterocyclyl group, any of which may be unsubstituted or substituted by (C1-C6)alkyl, (C1-C6)alkoxy, hydroxy, mercapto, (C1-C6)alkylthio, amino, halo (including fluoro, chloro, bromo and iodo), trifluoromethyl, cyano, nitro, —COOH, —CONH2, —COORA, —NHCORA, —CONHRA, NHRA, —NRARB, or —CONRARB wherein RA and RB are independently a (C1-C6)alkyl group, and ALK represents a straight or branched divalent C1-C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radical, and may be interrupted by one or more non-adjacent —NH—, —O— or —S—linkages, X represents —NH—, —O— or —S—, and m and n are independently 0 or 1; and A represents a group as defined in the specification.

  一种用于治疗人类和非人哺乳动物细菌感染的方法，包括向患有这种感染的受试者施用化合物(I)的抗细菌有效剂量或其药学或兽医学上可接受的盐：其中：R1代表氢，或者C1-C6烷基或C1-C6烷基取代一个或多个卤素原子；R2代表一个基团R10—(X)n—(ALK)m—其中R10代表氢，或者C1-C6烷基，C2-C6烯基，C2-C6炔基，环烷基，芳基或杂环烷基，任何一个都可以未取代或被(C1-C6)烷基，(C1-C6)烷氧基，羟基，巯基，(C1-C6)烷基硫基，氨基，卤素（包括氟，氯，溴和碘），三氟甲基，氰基，硝基，—COOH，—CONH2，—COORA，—NHCORA，—CONHRA，NHRA，—NRARB或—CONRARB取代，其中RA和RB独立地为(C1-C6)烷基，ALK代表直链或支链的二价C1-C6烷基，C2-C6烯基或C2-C6炔基基团，可以被一个或多个非相邻的—NH—，—O—或—S—连接所中断，X代表—NH—，—O—或—S—，m和n独立地为0或1；A代表规范中定义的一个基团。
• [EN] ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTERIENS
  申请人：BRITISH BIOTECH PHARM

  公开号：WO1999039704A1

  公开（公告）日：1999-08-12

  Compounds of formula (I) are antibacterials: wherein R1 represents hydrogen, or C1-C6 alkyl or C1-C6 alkyl substituted by one or more halogen atoms; R2 represents a group R10-(X)n-(ALK)M- wherein R10 represents hydrogen, or a C1-C6 alkyl, C2-C6 alkenyl,C2-C6 alkynyl, cycloalkyl, aryl, or heterocyclyl group, any of which may be unsubstituted or substituted by (C1-C6) alkyl, (C1-C6) alkoxy, hydroxy, mercapto, (C1-C6) alkylthio, amino, halo (including fluoro, chloro, bromo and iodo), trifluoromethyl, cyano, nitro, -COOH, -CONH2, -COORA, -NHCORA, -CONHR?A, -NHRA, -NRARB¿, or -CONRARB wherein R?A and RB¿ are independently a (C¿1?-C6) alkyl group, and ALK represents a straight or branched divalent C1-C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radical, and may be interrupted by one or more non-adjacent -NH-, -O- or -S- linkages, X represents -NH-, -O- or -S-, and m and n are independently 0 or 1; and A represents a group as defined in the specification.

  式(I)的化合物为抗菌剂，其中R1代表氢，或C1-C6烷基或C1-C6烷基取代的一个或多个卤素原子；R2代表一个基团R10-(X)n-(ALK)M-，其中R10代表氢，或C1-C6烷基，C2-C6烯基，C2-C6炔基，环烷基，芳基或杂环基，任何一个都可以是未取代或取代的(C1-C6)烷基，(C1-C6)烷氧基，羟基，巯基，(C1-C6)烷硫基，氨基，卤素（包括氟，氯，溴和碘），三氟甲基，氰基，硝基，-COOH，-CONH2，-COORA，-NHCORA，-CONHR?A，-NHRA，-NRARB¿，或者 -CONRARB，其中R?A和RB¿独立地为(C¿1?-C6)烷基，ALK代表直链或支链的二价C1-C6亚烷基，C2-C6烯基或C2-C6炔基基团，并且可以被一个或多个不相邻的-NH-，-O-或-S-连接所中断，X代表-NH-，-O-或-S-，m和n独立地为0或1；A代表规范中定义的一个基团。
• ANTIBACTERIAL AGENTS
  申请人：Vernalis (Oxford) Ltd

  公开号：EP1052984B1

  公开（公告）日：2004-05-12
• US6423690B1
  申请人：——

  公开号：US6423690B1

  公开（公告）日：2002-07-23
• US6787522B2
  申请人：——

  公开号：US6787522B2

  公开（公告）日：2004-09-07