(S)-1-cbz-3-吡咯烷羧酰胺 | 573704-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-cbz-3-吡咯烷羧酰胺
• 中文别名: (S)-1-CBZ-3-吡咯烷甲酰胺
• 英文名称: (+)-(S)-3-carbamidopyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (S)-3-carbamoylpyrrolidine-1-carboxylate；(S)-1-Cbz-3-pyrrolidinecarboxamide；benzyl (3S)-3-carbamoylpyrrolidine-1-carboxylate
• CAS: 573704-57-1
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: RFMDNYSGEQPCAA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-cbz-3-吡咯烷羧酰胺 在 劳森试剂 、 lithium hydroxide monohydrate 、 氢溴酸 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 83.0h， 生成 N-((2S,3R)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-1-phenylbutan-2-yl)-3-((S)-3-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl)benzamide
  参考文献：
  名称：

  Design of novel HIV-1 protease inhibitors incorporating isophthalamide-derived P2-P3 ligands: Synthesis, biological evaluation and X-ray structural studies of inhibitor-HIV-1 protease complex

  摘要：

  Based upon molecular insights from the X-ray structures of inhibitor-bound HIV-1 protease complexes, we have designed a series of isophthalamide-derived inhibitors incorporating substituted pyrrolidines, piperidines and thiazolidines as P2-P3 ligands for specific interactions in the S2-S3 extended site. Compound 4b has shown an enzyme K-i of 0.025 nM and antiviral IC50 of 69 nM. An X-ray crystal structure of inhibitor 4b-HIV-1 protease complex was determined at 1.33 angstrom resolution. We have also determined X-ray structure of 3b-bound HIV-1 protease at 1.27 angstrom resolution. These structures revealed important molecular insight into the inhibitor-HIV-1 protease interactions in the active site. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.04.005
• 作为产物：
  描述：

  (S)-1-N-Cbz-3-氰基吡咯烷 在 水 、 双氧水 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以55%的产率得到(S)-1-cbz-3-吡咯烷羧酰胺
  参考文献：
  名称：

  [EN] CARBAPENEM ANTIBACTERIALS WITH GRAM-NEGATIVE ACTIVITY
  [FR] AGENTS ANTIBACTÉRIENS DE CARBAPÉNEM AVEC ACTIVITÉ ANTI-GRAM NÉGATIF

  摘要：

  公开号：

  WO2011160020A3

文献信息

• Synthesis of Potent Oxindole CDK2 Inhibitors
  作者：Apos Dermatakis、Kin-Chun Luk、Wanda DePinto

  DOI：10.1016/s0968-0896(03)00036-1

  日期：2003.4

  A series of oxindole CDK2 inhibitors was synthesized. These novel analogues have a saturated monosubstituted cyclic moiety at their C-4 position that mimics the ribofuranoside of ATP. This substitution afforded agents with increased potency relative to the parent indolinone and nanomolar range IC50 against the CDK2 enzyme and two cancer cell lines. (C) 2003 Elsevier Science Ltd. All rights reserved.
• CARBAPENEM ANTIBACTERIALS WITH GRAM-NEGATIVE ACTIVITY
  申请人：FOB Synthesis, Inc.

  公开号：EP2590978B1

  公开（公告）日：2017-09-20
• Carbapenem Antibacterials with Gram-Negative Activity
  申请人：FOB Synthesis, Inc.

  公开号：US20130172313A1

  公开（公告）日：2013-07-04

  The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment.
• US9149461B2
  申请人：——

  公开号：US9149461B2

  公开（公告）日：2015-10-06