6-n-propylandrosta-1,4,6-triene-3,17-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-n-propylandrosta-1,4,6-triene-3,17-dione
• 英文别名: (8R,9S,10R,13S,14S)-10,13-dimethyl-6-propyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthrene-3,17-dione
• 化学式: C₂₂H₂₈O₂
• 分子量: 324.463
• InChiKey: LKOTWAQBXMBDFM-BDCMKUQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (8R,9S,10R,13S,14S)-10,13-Dimethyl-6-propyl-1,8,9,10,11,12,13,14,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 8.0h， 以51%的产率得到6-n-propylandrosta-1,4,6-triene-3,17-dione
  参考文献：
  名称：

  6-Alkylandrosta-4,6-diene-3,17-diones and their 1,4,6-triene analogs as aromatase inhibitors

  摘要：

  Two series of 6-alkylandrosta-4,6-diene-3,17-diones (5) and their 1,4,6-triene analogs 6 were synthesized as aromatase inhibitors to gain insight into the structure-activity relationship between varying the 6-n-alkyl substituents (C-1-C-7) and inhibitory activity. All of the steroids synthesized were extremely powerful competitive inhibitors of aromatase in human placental microsomes, with apparent K-i values for the 6-alkyl-4,6-diene steroids 5 ranging from 17 to 36 nM and with those for the 1,4,6-triene steroids 6 ranging from 2.5 to 58 nM. The 6-ethyl-1,4,6-triene compound 6b (K-i = 2.5 nM) was the most potent inhibitor among them. The 6-alkyl-1,4,6-triene steroids 6, except for the 6-methyl analog 6a, had higher affinity for aromatase than the natural substrate androstenedione (K-m = 24 nM), and their inhibitory activities were more potent than the corresponding 4,6-diene steroids 5. In a series of the 4,6-diene steroids 5, compounds 5c-f with the n-alkyl chain substituents (C-3 to C-6) also had slightly higher affinity than androstenedione for aromatase. All of the 1,4,6-triene steroids 6 inactivated aromatase in a time-dependent manner, with k(inact) values ranging from 0.021 to 0.074 min(-1); in contrast, the 4,6-diene analogs 5 did not. The inactivation was prevented by androstenedione, and no significant effect of L-cysteine on the inactivation was observed in each case. These results indicate that the length of the n-alkyl substituent at C-6 of androsta-1,4,6-triene-3,17-dione (6h), rather than its 4,6-diene analog 5h, plays a critical role in tight binding to the active site of aromatase. No significant correlation was observed between affinity for the enzyme and the inactivation ability of the 6-alkyl-1,4,6-trienes. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)86814-6

文献信息

• Iron catalyzed methylation and ethylation of vinyl arenes
  作者：Nengbo Zhu、Jianguo Zhao、Hongli Bao

  DOI：10.1039/c6sc04274k

  日期：——

  Short alkyl chain Heck (type) reactions, especially methyl Heck reactions, are a difficult aspect of the alkyl Heck reaction. To provide a solution to this problem, iron-catalyzed methyl, ethyl and propyl Heck reactions were developed using readily available alkyl peroxides as alkyl sources. The reaction conditions were mild, clean, and easy to handle. No additive was needed, and no hazardous waste

  短烷基链Heck（类型）反应，尤其是甲基Heck反应，是烷基Heck反应的一个困难方面。为了解决该问题，使用容易获得的烷基过氧化物作为烷基源，开发了铁催化的甲基，乙基和丙基Heck反应。反应条件温和，清洁且易于处理。无需添加剂，也不会产生危险废物。在大多数情况下，获得的一种异构体的收率高达99％。该反应适用于多种类型的烯烃，并能耐受各种官能团。进行了天然产物和药物分子的几个后期功能化，以证明该反应的合成应用。