4-cyclopentyl-1-iodo-1-trans-buten-3-ol | 55444-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-cyclopentyl-1-iodo-1-trans-buten-3-ol
• 英文别名: 4-cyclopentyl-1iodo-1-trans-buten-3-ol；(E)-1-cyclopentyl-4-iodobut-3-en-2-ol
• CAS: 55444-52-5
• 化学式: C₉H₁₅IO
• 分子量: 266.122
• InChiKey: QYCRZWRPFOOMOA-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-cyclopentyl-1-iodo-1-trans-buten-3-ol 在 copper(l) iodide 、 四(三苯基膦)钯 、 nickel boride 、 氢气 作用下， 以 二乙胺 为溶剂， 反应 3.0h， 生成 (11Z,13E)-15-hydroxy-16-cyclopentylhexadeca-11,13-dienoic acid
  参考文献：
  名称：

  Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogs

  摘要：

  The structural requirements for inhibition of RBL-1 (rat basophilic leukemia) 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15-HETE, 1) were studied by systematic chemical modifications of the molecule at the hydroxyl and carboxyl groups, the double bonds, and the carboxylate and omega side chains. The most potent inhibitors were analogues that contained a 5,8-cis,cis-diene system and acted as alternate substrates for the enzyme. However, several analogues in which the 5,8-diene had been reduced were also found to inhibit the enzyme. Inhibition of 5-lipoxygenase by 15-hydroxyeicosa-11,13-dienoic acid (15-HEDE) analogues was optimal in compounds that generally contained a free carboxyl group, a carboxylate side chain of nine carbons, an omega side chain of five or six carbons, a cis,trans- or trans,cis-11,13-diene or 11,13-diyne system, and a 15-hydroxyl group. Conversion of 15-HEDE to its 16-membered lactone reduced but did not eliminate 5-lipoxygenase inhibitory activity. In contrast, a 3- to 10-fold enhancement of activity occurred when 5,15-diHETE (58) or 5-HETE (56) were cyclized to their respective delta-lactones. Molecular modeling of 15-HEDE analogues, modified in the C11-C15 region, showed that inactive analogues protrude into regions in space not occupied by active analogues. These structural studies indicate that multiple regions are important for 5-lipoxygenase inhibition by both 15-HETE and 15-HEDE analogues and that no single region plays a predominant role in inhibition.

  DOI：

  10.1021/jm00385a005
• 作为产物：
  描述：

  4-cyclopentyl-1-iodo-1-trans-buten-3-one 在 sodium borohydrid 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 为溶剂， 生成 4-cyclopentyl-1-iodo-1-trans-buten-3-ol
  参考文献：
  名称：

  Novel 11-alkoxy-9-keto (or hydroxy)-prostenoic acid derivatives and

  摘要：

  本公开描述了某些11-烷氧基-9-酮（或羟基）-前列酸衍生物，可用作抗微生物药剂、降压药剂、抗溃疡药剂或中间体。

  公开号：

  US04236027A1

文献信息

• Cycloalkyl and cycloalkenyl prostaglandin congeners
  申请人：American Cyanamid Company

  公开号：US04076947A1

  公开（公告）日：1978-02-28

  This disclosure describes novel 15-hydroxy prostanoic acids and derivatives thereof useful as bronchodilators, hypotensive agents and gastric acid secretion inhibitors (anti-ulcer).

  本公开揭示了作为支气管扩张剂、降压剂和胃酸分泌抑制剂（抗溃疡）有用的新型15-羟基前列腺酸及其衍生物。
• Novel prostaglandins
  申请人：American Cyanamid Company

  公开号：US04180677A1

  公开（公告）日：1979-12-25

  This disclosure describes novel 15-hydroxy prostanoic acid derivatives having anti-ulcer, bronchodilator, and hypotensive activity.

  这份披露描述了具有抗溃疡、支气管扩张和降压活性的新型15-羟基前列腺酸衍生物。
• HAVIV F.; RATAJCZYK J. D.; DENET R. W.; MARTIN Y. C.; DYER R. D.; CARTER +, J. MED. CHEM., 30,(1987) N 2, 254-263
  作者：HAVIV F.、 RATAJCZYK J. D.、 DENET R. W.、 MARTIN Y. C.、 DYER R. D.、 CARTER +

  DOI：——

  日期：——
• US3993674A
  申请人：——

  公开号：US3993674A

  公开（公告）日：1976-11-23
• US4076947A
  申请人：——

  公开号：US4076947A

  公开（公告）日：1978-02-28