(3S,6S,9aS)-6-(Naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester | 188127-66-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,6S,9aS)-6-(Naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3S,6S,9aS)-6-(naphthalen-1-ylsulfonylamino)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate
• CAS: 188127-66-4
• 化学式: C₂₄H₃₀N₂O₅S
• 分子量: 458.579
• InChiKey: YGWJYXHCJWKPOE-IHPCNDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,6S,9aS)-6-(Naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以93%的产率得到(3S,6S,9aS)-6-(Naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of conformationally constrained arginal thrombin inhibitors

  摘要：

  A series of conformationally constrained arginal thrombin inhibitors was prepared starting from 5,6 or 5,7 bicyclic lactamic structures, that an indirect approach of X-ray structure-based drug design indicated as D-Phe-Pro dipeptide mimetics. The tetrahydroquinolyl sulfonamido derivative Ig (LR-D/009) displayed the best inhibitory potency (IC50=0.018 mu m), with good selectivity over plasmin and trypsin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00403-4
• 作为产物：
  描述：

  (3S,6S,9aS)-6-Benzyloxycarbonylamino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (3S,6S,9aS)-6-(Naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of conformationally constrained arginal thrombin inhibitors

  摘要：

  A series of conformationally constrained arginal thrombin inhibitors was prepared starting from 5,6 or 5,7 bicyclic lactamic structures, that an indirect approach of X-ray structure-based drug design indicated as D-Phe-Pro dipeptide mimetics. The tetrahydroquinolyl sulfonamido derivative Ig (LR-D/009) displayed the best inhibitory potency (IC50=0.018 mu m), with good selectivity over plasmin and trypsin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00403-4

文献信息

• [EN] BICYCLIC LACTAM DERIVATIVES AS THROMBIN INHIBITORS<br/>[FR] DERIVES LACTAMES BICYCLIQUES UTILISES COMME INHIBITEURS DE THROMBINE
  申请人：A. MENARINI INDUSTRIE FARMACEUTICHE RIUNITE S.R.L.

  公开号：WO1997005160A1

  公开（公告）日：1997-02-13

  (EN) Bicyclic lactams containing an arginine residue, which can be of use in therapy as thrombin inhibitors, are disclosed.(FR) L'invention porte sur des lactames bicycliques contenant un reste arginine qui peuvent être utilisés, dans un traitement, comme inhibiteurs de thrombine.
• Design and synthesis of conformationally constrained arginal thrombin inhibitors
  作者：Aldo Salimbeni、Fabio Paleari、Renato Canevotti、Marco Criscuoli、Marco Criscuoli、Annalisa Lippi、Mauro Angiolini、Laura Belvisi、Carlo Scolastico、Lino Colombo

  DOI：10.1016/s0960-894x(97)00403-4

  日期：1997.9

  A series of conformationally constrained arginal thrombin inhibitors was prepared starting from 5,6 or 5,7 bicyclic lactamic structures, that an indirect approach of X-ray structure-based drug design indicated as D-Phe-Pro dipeptide mimetics. The tetrahydroquinolyl sulfonamido derivative Ig (LR-D/009) displayed the best inhibitory potency (IC50=0.018 mu m), with good selectivity over plasmin and trypsin. (C) 1997 Elsevier Science Ltd.