16β-methyl-1,4,6,8-pregnatetraene-17α,21-diol-3,11,20-trione 21-acetate | 73082-94-7

• 分子结构分类: 有机化合物
• 英文名称: 16β-methyl-1,4,6,8-pregnatetraene-17α,21-diol-3,11,20-trione 21-acetate
• 英文别名: [2-[(10S,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-3,11-dioxo-12,14,15,16-tetrahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 73082-94-7
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: QPMVKJKHPYBJTE-JJZCETQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  16β-methyl-1,4,6,8-pregnatetraene-11β,17α,21-triol-3,20-dione 21-acetate 在 二氧化锰 作用下， 以 二氯甲烷 为溶剂， 生成 16β-methyl-1,4,6,8-pregnatetraene-17α,21-diol-3,11,20-trione 21-acetate
  参考文献：
  名称：

  1,3,5(10),6,8,14-19-Nor-pregnahexaenes, their use as anti-psoriatic

  摘要：

  1,3,5(10),6,8,14-19 Nor-孕烯-20-酮表现出最小或没有激素活性的抗有丝分裂活性。它们在局部应用时特别有用于治疗和控制牛皮癣，16.alpha.-甲基-1,3,5(10),6,8,14-19-诺-孕烯-3,17.alpha.,21-三醇-20-酮 21-醋酸酯是一种首选的抗牛皮癣化合物。

  公开号：

  US04172132A1

文献信息

• 1,3,5(10),6,8-19-Nor-pregnapentaenes, their use as anti-psoriatic
  申请人：Schering Corporation

  公开号：US04185101A1

  公开（公告）日：1980-01-22

  1,3,5(10),6,8-19-Nor-pregnapentaene-20-ones exhibit anti-mitotic activity with minimal or no hormonal activity. They are particularly useful in the treatment and control of psoriasis when applied topically, preferred anti-psoriatic compounds being 1,3,5(10),6,8-19-nor-pregnapentaene-3,17.alpha.,21-triol-20-one 21-acetate and the 16.alpha.-methyl and 16.beta.-methyl analogs thereof. The 1,3,5(10),6,8-19-nor-pregnapentaene-20-ones are also useful as intermediates in the preparation of the corresponding 14-dehydro compounds which also exhibit anti-mitotic activity as described and claimed in copending application Ser. No. 819,182 filed July 26, 1977 of Richard W. Draper and Charles J. Casmer of common assignee as this application, and now abandoned.

  1,3,5(10),6,8-19-去孕五烯-20-酮具有最小或没有激素活性的抗有丝分裂活性。当局部应用时，它们特别有用于牛皮癣的治疗和控制，首选的抗牛皮癣化合物是1,3,5(10),6,8-19-去孕五烯-3,17α,21-三醇-20-酮21-乙酸酯和其16α-甲基和16β-甲基类似物。1,3,5(10),6,8-19-去孕五烯-20-酮也可用作制备相应的14-去氢化合物的中间体，这些化合物如同本申请的共同申请人Richard W. Draper和Charles J. Casmer于1977年7月26日提交的申请号为819,182的申请中所述和声明，并已被弃用。
• Novel 19-nor-pregnahexaenes, process for the preparation thereof, and pharmaceutical compositions containing them
  申请人：Technobiotic Ltd.

  公开号：EP0000609A1

  公开（公告）日：1979-02-07

  19-Nor-pregnahexaenes of formula wherein A is hydrogen, lower alkyl, fluoro or fluoro- substituted methyl; R1 is hydrogen, lower alkyl, or an acyl radical of a carboxylic acid; W is (H,H); (H, lower alkyl); (H, α-OR2), with R2 being hydrogen or an acyl radical of a carboxylic acid; or - CHT, with T being hydrogen, lower alkyl, fluorine, or chlorine; Q is OR4, with R4 being hydrogen or an acyl radical of a carboxylic acid; hydrogen, provided W is (H,H) or (H, lower alkyl); or together with W represents a 16α, 17α-lower alkylidenedioxy grouping; Y is (H,H), (H,OH), or oxygen; Z is hydrogen, chlorine or bromine; R, is hydrogen or an acyl radical of a carboxylic acid; or OR3 together with Q represents an alkylidenedioxy or alkylorthoalkanoate grouping; and when Q is hydroxy and R3 is hydrogen, the 17a, 20; 20, 21-bismethylanedioxy derivatives thereof; These compounds are novel, with the exception of the 21-acetate and 3,21-diacetate of 19-nor-pregna- 1,3,5 (10), 6,8,14- hexanene-3,17a,21- triol-20-one, while pharmaceutical compositions containing the latter two compounds are also novel. The preparation of the novel compounds by three methods is described, in particular dehydrogenation in position 14 of appropriate 19-nor-pregna- 1,3,5(10), 6,8-pentaenes by DDq. Representative compounds of the inventions have been shown to exhibit antimitotic activity and, in particular, are useful in treating psoriasis.

  式中的 19-正regnahexaenes 其中 A 是氢、低级烷基、氟或氟取代的甲基； R1 是氢、低级烷基或羧酸酰基； W 是（H，H）；（H，低级烷基）；（H，α-OR2），其中 R2 是氢或羧酸酰基；或 - CHT，其中 T 是氢、低级烷基、氟或氯；Q 是 OR4，其中 R4 是氢或羧酸酰基；氢，条件是 W 是（H，H）或（H，低级烷基）；或与 W 一起代表 16α、17α-低级亚烷基二氧基基团； Y 是（H,H）、（H,OH）或氧； Z 是氢、氯或溴； R，是氢或羧酸酰基；或 OR3 与 Q 一起代表亚烷基二氧基或烷基正烷酸酯基团； 以及当 Q 为羟基且 R3 为氢时，其 17a、20；20、21-二烷基二氧基衍生物； 除了 19-去甲-1,3,5(10),6,8,14-己烯-3,17a,21-三醇-20-酮的 21-乙酸酯和 3,21-二乙酸酯之外，这些化合物都是新颖的，而含有后两种化合物的药物组合物也是新颖的。本发明介绍了通过三种方法制备新型化合物，特别是通过 DDq 在适当的 19-去氢-1,3,5(10),6,8-戊烯的第 14 位进行脱氢。本发明中具有代表性的化合物已被证明具有抗变态反应活性，特别是可用于治疗牛皮癣。
• US4172132A
  申请人：——

  公开号：US4172132A

  公开（公告）日：1979-10-23
• US4185101A
  申请人：——

  公开号：US4185101A

  公开（公告）日：1980-01-22