[3,5-difluoro-4-(tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester | 590420-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3,5-difluoro-4-(tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester
• 英文别名: isobutyl [4-(tetrahydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]carbamate；2-methylpropyl N-[3,5-difluoro-4-(thian-4-yl)phenyl]carbamate
• CAS: 590420-99-8
• 化学式: C₁₆H₂₁F₂NO₂S
• 分子量: 329.411
• InChiKey: XKZLTQHXNIIOAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3,5-difluoro-4-(tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 trans-[3,5-difluoro-4-(1-oxo-tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester
  参考文献：
  名称：

  Antibacterial Oxazolidinones Possessing a Novel C-5 Side Chain. (5R)-trans-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic Acid Amide (PF-00422602), a New Lead Compound

  摘要：

  Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus possess less potential for the side effects associated with MAO inhibition. The title compound (14) showed reduced in vivo myelotoxicity compared to linezolid in a 14-day safety study in rats, potent in vivo efficacy in murine systemic infection models, and excellent pharmacokinetic properties.

  DOI：

  10.1021/jm070708p
• 作为产物：
  描述：

  [4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]carbamic acid isobutyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 115.2h， 生成 [3,5-difluoro-4-(tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester
  参考文献：
  名称：

  N-aryl-2-oxazolidinone-5-carboxamides and their derivatives

  摘要：

  本发明提供了具有以下式I、II和III的抗菌剂。

  公开号：

  US20040147760A1

文献信息

• N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
  申请人：——

  公开号：US20040147760A1

  公开（公告）日：2004-07-29

  The present invention provides antibacterial agents having the formulae I, II, and III described herein.

  本发明提供了具有以下式I、II和III的抗菌剂。
• [EN] N-ARYL-2-OXAZOLIDINONE-5-CARBOXAMIDES AND THEIR DERIVATIVES AND THEIR USE AS ANTIBACTERIALS<br/>[FR] N-ARYL-2-OXAZOLIDINONE-5-CARBOXAMIDES ET LEURS DERIVES ET UTILISATION DE CES COMPOSES COMME ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2003072553A1

  公开（公告）日：2003-09-04

  Compounds of formula B-C-A-CO-NH-R1, wherein A is structure i, ii or iii: formulae (I), (II), (III). C is optionally substituted aryl or heteroaryl, and B is a specified cyclic moiety, or C and B together are a heterobicyclic moiety, are useful as antibacterial agents.

  公式为B-C-A-CO-NH-R1的化合物，其中A是结构i、ii或iii：公式(I)、(II)、(III)。C是可选择取代的芳基或杂环芳基，而B是特定的环状基团，或者C和B一起是一个杂双环基团，可用作抗菌剂。
• US7645781B2
  申请人：——

  公开号：US7645781B2

  公开（公告）日：2010-01-12
• Antibacterial Oxazolidinones Possessing a Novel C-5 Side Chain. (5<i>R</i>)-<i>trans</i>-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic Acid Amide (PF-00422602), a New Lead Compound
  作者：Toni-Jo Poel、Richard C. Thomas、Wade J. Adams、Paul A. Aristoff、Michael R. Barbachyn、Frederick E. Boyer、Joan Brieland、Roger Brideau、Joanne Brodfuehrer、Alan P. Brown、Allison L. Choy、Michael Dermyer、Michael Dority、Charles W. Ford、Robert C. Gadwood、Debra Hanna、Cai Hongliang、Michael D. Huband、Christopher Huber、Rose Kelly、Ji-Young Kim、Joseph P. Martin、Paul J. Pagano、Daniel Ross、Laura Skerlos、Mark C. Sulavik、Tong Zhu、Gary E. Zurenko、J. V. N. Vara Prasad

  DOI：10.1021/jm070708p

  日期：2007.11.1

  Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus possess less potential for the side effects associated with MAO inhibition. The title compound (14) showed reduced in vivo myelotoxicity compared to linezolid in a 14-day safety study in rats, potent in vivo efficacy in murine systemic infection models, and excellent pharmacokinetic properties.