3-(4-Iodo-butyl)-4H-[1,2,4]oxadiazol-5-one | 219536-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-Iodo-butyl)-4H-[1,2,4]oxadiazol-5-one
• 英文别名: 3-(4-iodobutyl)-4H-1,2,4-oxadiazol-5-one
• CAS: 219536-38-6
• 化学式: C₆H₉IN₂O₂
• 分子量: 268.054
• InChiKey: DJMINHCNYACWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-Iodo-butyl)-4H-[1,2,4]oxadiazol-5-one 在 六甲基磷酰三胺 、 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 2-((1S,2R)-2-Hydroxy-cyclopentyl)-6-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-hexanoic acid ethyl ester
  参考文献：
  名称：

  5,5-Trans lactone-containing inhibitors of serine proteases: Identification of a novel, acylating thrombin inhibitor

  摘要：

  Synthesis of a variety of 5,5-trans fused lactones, related to compounds found in extracts of Lantana camara, has provided a series of novel acylating inhibitors of human thrombin, trypsin, chymotrypsin and human leucocyte elastase. The most effective thrombin inhibitor is 7 with an IC50 of 130nM and a K-obs/[I] of 4,000 M-1 s(-1). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00531-9
• 作为产物：
  描述：

  1-Iodo-5-nitro-pentane 在 氢氧化钾 、 异氰酸苯酯 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 3-(4-Iodo-butyl)-4H-[1,2,4]oxadiazol-5-one
  参考文献：
  名称：

  5,5-Trans lactone-containing inhibitors of serine proteases: Identification of a novel, acylating thrombin inhibitor

  摘要：

  Synthesis of a variety of 5,5-trans fused lactones, related to compounds found in extracts of Lantana camara, has provided a series of novel acylating inhibitors of human thrombin, trypsin, chymotrypsin and human leucocyte elastase. The most effective thrombin inhibitor is 7 with an IC50 of 130nM and a K-obs/[I] of 4,000 M-1 s(-1). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00531-9

文献信息

• Thrombin inhibitors based on [5,5] trans-fused indane lactams
  作者：Martin Pass、Said Abu-Rabie、Andrew Baxter、Richard Conroy、Steven J Coote、Andrew P Craven、Harry Finch、Seán Hindley、Henry A Kelly、Andrew W Lowdon、Edward McDonald、William L Mitchell、Neil A Pegg、Pan A Procopiou、Nigel G Ramsden、Rhian Thomas、Dawn A Walker、Nigel S Watson、Harren Jhoti、Christopher J Mooney、Chi-Man Tang、Pamela J Thomas、Simon Parry、Champa Patel

  DOI：10.1016/s0960-894x(99)00244-9

  日期：1999.6

  A series of trans-fused lactams containing the indane nucleus has been prepared. Compound 19 has much enhanced plasma stability compared with its lactone counterpart and shows appreciable in vitro anticoagulant activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthetic [5,5] trans-fused indane lactones as inhibitors of thrombin
  作者：Martin Pass、Richard E. Bolton、Steven J. Coote、Harry Finch、Sean Hindley、Andrew Lowdon、Edward McDonald、Jessica McLaren、Martin Owen、Neil A. Pegg、Christopher J. Mooney、Chi-Man Tang、Simon Parry、Champa Patel

  DOI：10.1016/s0960-894x(99)00002-5

  日期：1999.2

  Synthesis of trans-fused lactones containing; the indane nucleus has resulted in a series of potent acylating inhibitors of thrombin. As an er;ample compound Ile has an apparent second order rate constant of 11x10(6) M(-1)sec(-1) for the inhibition of thrombin. The anticoagulant activity of these compounds is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• METHOD OF INHIBITING SERINE PROTEASE ENZYMES
  申请人：GLAXO GROUP LIMITED

  公开号：EP1015454A1

  公开（公告）日：2000-07-05
• PYRROLOPYRROLIDINE DERIVATIVES AND THEIR USE AS SERINE PROTEASE INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1015456A1

  公开（公告）日：2000-07-05
• [EN] PYRROLOPYRROLIDINE DERIVATIVES AND THEIR USE AS SERINE PROTEASE INHIBITORS<br/>[FR] DERIVES DE PYRROLOPYRROLIDINE ET LEUR UTILISATION COMME INHIBITEURS DE SERINE PROTEASE
  申请人：GLAXO GROUP LIMITED

  公开号：WO1999012935A1

  公开（公告）日：1999-03-18

  (EN) There is provided according to the invention an inhibitor of a serine protease enzyme which is a substituted derivative of trans-hexahydropyrrolo[3,4-b]pyrrol-2-one.(FR) L'invention concerne un inhibiteur d'une enzyme de sérine protéase qui est un dérivé substitué de trans-hexahydropyrrolo[3,4-b]pyrrol-2-one.