Cyclopentyl 4-pyridylacetate | 130275-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Cyclopentyl 4-pyridylacetate
• 英文别名: Pyridin-4-yl-acetic acid cyclopentyl ester；cyclopentyl 2-pyridin-4-ylacetate
• CAS: 130275-94-4
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: WRJKRKBRDCTLLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-4-乙酸甲酯 、 环戊醇 在 正丁基锂 作用下， 生成 Cyclopentyl 4-pyridylacetate
  参考文献：
  名称：

  Inhibition of enzymes of estrogen and androgen biosynthesis by esters of 4-pyridylacetic acid

  摘要：

  A variety of esters of 4-pyridylacetic acid have been prepared by base mediated exchange from the methyl ester. Several of the esters of alcohols that contained a cyclohexyl ring were potent inhibitors of human placental aromatase and of the rat testicular 17 alpha-hydroxylase/C17-20lyase complex. The most potent agents found against both enzyme complexes were the borneyl, isopinocampheyl, and 1-adamantyl esters. These were over 100 times more potent than aminoglutethimide against aromatase and of greater potency than ketoconazole against hydroxylase/lyase. Potency against either enzyme complex was reduced if the ester function was borne on the cyclohexyl ring in an axial rather than an equatorial position. Some differential selectivity could be introduced since whereas methyl substitution adjacent to the carbonyl group reduced the inhibition of aromatase, it increased that against hydroxylase/lyase.

  DOI：

  10.1021/jm00173a022

文献信息

• Cycloalkyl-substituted 4-pyridyl derivatives and process for their preparation
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0253681A2

  公开（公告）日：1988-01-20

  The invention relates to cycloalkyl-substituted 4-pyridyl deri­vatives of formula (I) wherein R is C₁-C₄ alkyl; each of R₁ and R₂ is, independently, hydrogen or C₁-C₄ alkyl; n is an integer of 1 to 5; and either (a) A is >C=O and B is -O-, -NH- or -CH₂-; or (b) A is -CH₂- and B is -O-, -NH-, -CH₂- or >C=O; or (c) A is -O- and B is >C=O or -CH₂-; or (d) A is -NH- and B is >C=O or -CH₂-, and their pharmaceutically acceptable salts. The compounds of the invention show aromatase inhibiting activity and can be useful, e.g., in treating hormone-dependent tumors and prostatic hyperplasia.

  本发明涉及式 (I) 的环烷基取代的 4-吡啶基衍生物 其中 R₁-C₄ 烷基； R₁ 和 R₂ 各自独立地为氢或 C₁-C₄ 烷基； n 是 1 至 5 的整数；并且 (a) A 为 >C=O，B 为 -O-、-NH- 或 -CH₂-；或 (b) A 是-CH₂-，B 是-O-、-NH-、-CH₂- 或 >C=O；或 (c) A 为-O-，B 为 >C=O 或-CH₂-；或 (d) A 为-NH-，B 为 >C=O 或-CH₂-、 及其药学上可接受的盐类。 本发明的化合物具有芳香化酶抑制活性，可用于治疗激素依赖性肿瘤和前列腺增生症等。
• US4797411A
  申请人：——

  公开号：US4797411A

  公开（公告）日：1989-01-10
• Inhibition of enzymes of estrogen and androgen biosynthesis by esters of 4-pyridylacetic acid
  作者：Raymond McCague、Martin G. Rowlands、S. Elaine Barrie、John Houghton

  DOI：10.1021/jm00173a022

  日期：1990.11

  A variety of esters of 4-pyridylacetic acid have been prepared by base mediated exchange from the methyl ester. Several of the esters of alcohols that contained a cyclohexyl ring were potent inhibitors of human placental aromatase and of the rat testicular 17 alpha-hydroxylase/C17-20lyase complex. The most potent agents found against both enzyme complexes were the borneyl, isopinocampheyl, and 1-adamantyl esters. These were over 100 times more potent than aminoglutethimide against aromatase and of greater potency than ketoconazole against hydroxylase/lyase. Potency against either enzyme complex was reduced if the ester function was borne on the cyclohexyl ring in an axial rather than an equatorial position. Some differential selectivity could be introduced since whereas methyl substitution adjacent to the carbonyl group reduced the inhibition of aromatase, it increased that against hydroxylase/lyase.