tert-butyl N-[(2S)-1-(3-chloropropylsulfonylamino)-3,3-dimethylbutan-2-yl]carbamate | 1131731-52-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: tert-butyl N-[(2S)-1-(3-chloropropylsulfonylamino)-3,3-dimethylbutan-2-yl]carbamate
• CAS: 1131731-52-6
• 化学式: C₁₄H₂₉ClN₂O₄S
• 分子量: 356.914
• InChiKey: RWEFIHJSRPANLI-LLVKDONJSA-N

物化性质

• 密度：
  1.137±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-(3-chloropropylsulfonylamino)-3,3-dimethylbutan-2-yl]carbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl N-[(2S)-1-(1,1-dioxo-1,2-thiazolidin-2-yl)-3,3-dimethylbutan-2-yl]carbamate
  参考文献：
  名称：

  Novel potent inhibitors of hepatitis C virus (HCV) NS3 protease with cyclic sulfonyl P3 cappings

  摘要：

  Extensive SAR studies of the P3 capping group led to the discovery of a series of potent inhibitors with sultam and cyclic sulfonyl urea moieties as the P3 capping. The bicyclic thiophene-sultam or phenyl- sultam cappings were selected for further SAR development. Modi. cation at the P3 side chain determined that the tert-butyl group was the best choice at that position. Optimization of P1 residue significantly improved potency and selectivity. The combination of optimal moieties at all positions led to the discovery of compound 33. This compound had the best overall pro. le in potency and PK profile: excellent K-i* of 5.3 nM and activity in replicon (EC90) of 80 nM, extremely high selectivity of 6100, and a good rat PO AUC of 1.43 mu Mh. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.111
• 作为产物：
  描述：

  3-氯丙烷磺酰氯 、 [(2S)-1-氨基-3,3-二甲基-2-丁烷基](2-甲基-2-丙基)氨基甲酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl N-[(2S)-1-(3-chloropropylsulfonylamino)-3,3-dimethylbutan-2-yl]carbamate
  参考文献：
  名称：

  Novel potent inhibitors of hepatitis C virus (HCV) NS3 protease with cyclic sulfonyl P3 cappings

  摘要：

  Extensive SAR studies of the P3 capping group led to the discovery of a series of potent inhibitors with sultam and cyclic sulfonyl urea moieties as the P3 capping. The bicyclic thiophene-sultam or phenyl- sultam cappings were selected for further SAR development. Modi. cation at the P3 side chain determined that the tert-butyl group was the best choice at that position. Optimization of P1 residue significantly improved potency and selectivity. The combination of optimal moieties at all positions led to the discovery of compound 33. This compound had the best overall pro. le in potency and PK profile: excellent K-i* of 5.3 nM and activity in replicon (EC90) of 80 nM, extremely high selectivity of 6100, and a good rat PO AUC of 1.43 mu Mh. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.111

文献信息

• [EN] NOVEL KETOAMIDES WITH CYCLIC P4'S AS INHIBITORS OF NS3 SERINE PROTEASE OF HEPATITIS C VIRUS<br/>[FR] NOUVEAUX CETOAMIDES A P4 CYCLIQUES EN TANT QU'INHIBITEURS DE LA NS3 SERINE PROTEASE DU VIRUS DE L'HEPATITE C
  申请人：SCHERING CORP

  公开号：WO2005085242A1

  公开（公告）日：2005-09-15

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

  本发明公开了具有HCV蛋白酶抑制活性的新化合物，以及制备这种化合物的方法。在另一实施方式中，该发明公开了包含这种化合物的药物组合物，以及使用它们治疗与HCV蛋白酶相关的疾病的方法。
• EP1730142B1
  申请人：——

  公开号：EP1730142B1

  公开（公告）日：2011-06-29