9α,11β-dichloro-17α,21-dihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 21-acetate | 73082-60-7

• 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: 9α,11β-dichloro-17α,21-dihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 21-acetate
• 英文别名: 9α,11β-dichloro-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 21-acetate；[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9,11-dichloro-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 73082-60-7
• 化学式: C₂₄H₃₀Cl₂O₅
• 分子量: 469.405
• InChiKey: CUUMYFDKBCFMEN-QZIXMDIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 9α,11β-dichloro-17α,21-dihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 21-acetate 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以0.1 g的产率得到9α,11β-dichloro-17α,21-dihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17-(2'-furoate) 21-acetate
  参考文献：
  名称：

  皮质类固醇17-杂环芳族酯的合成及结构活性研究。1. 9 alpha，11 beta-dichloro系列。

  摘要：

  描述了一系列9α，11β-二氯-16-甲基皮质类固醇17-杂芳基羧酸盐的制备和局部抗炎作用。在4-（二甲基氨基）吡啶存在下，通过用适当的杂芳基羰基氯直接酰化将17-酰基引入9α，11β-二氯21-乙酸酯中。或者，将21-官能化的17-羟基δ9（11）化合物在17酰化，然后进行C-环氯化。研究最广泛的杂环酰基官能团是2-糠酰基，但是还研究了3-糠酰基以及2-和3-壬酰基衍生物。通过对Tonelli巴豆油耳测定法进行5天修改，测量了小鼠的抗炎能力。最有效的局部抗炎化合物是16个α-甲基系列中的17个杂芳基酯，其中21个取代基是氯或氟。因此，2p [21-氯17-（2'-糠酸酯）]的效力是戊酸倍他米松的8倍，而2s [21-氟17-（2'-糠酸酯）]，2r [21-氯17-（2'-糠酸酯）]，2r [21-氯17-（2'-糠酸酯）]。 -theonate）]和2v [6α-氟21-氯17-（2'

  DOI：

  10.1021/jm00389a017

文献信息

• Novel process for the preparation of steroidal esters
  申请人：Plurichemie Anstalt

  公开号：US04655971A1

  公开（公告）日：1987-04-07

  A process for the preparation of corticosteriod esters of the formula ##STR1## in which ---- signifies that a double bond can be present; X is hydrogen, chlorine or fluorine; R.sub.1 is hydrogen, fluorine, chlorine or methyl, which may be either .alpha. or .beta.; R.sub.2 is halogen, oxo or hydroxyl; or R.sub.3 is hydrogen, .alpha.-methyl or .beta.-methyl; or R.sub.2 and X jointly form an epoxide group; R.sub.4 is an acyl group of the formula RCO, in which R is one of the following (i) an alkyl group containing 1 to 16 carbon atoms, whether straight-chained, branched or cyclic; (ii) an aralkyl group of 7 to 8 carbon atoms; (iii) a phenyl group; R.sub.5 is hydroxyl or R.sub.6 ; where R.sub.6 is hydrogen, one or two halogen atom substituents or OR.sub.7, where R.sub.7 is an acyl group of the formula R'CO in which R', which can be identical or different to R in the same molecule, is one of the following: (i) an alkyl group of 1 to 16 carbon atoms, whether straight-chained, branched or cyclic; (ii) an aralkyl group of 7 to 8 carbon atoms; or (iii) a phenyl group. which comprises esterifying a compound of the formula ##STR2## wherein X, R.sub.1, R.sub.3 and R.sub.5 are as defined above, and R.sub.8 is trihaloacetate, halogen or oxo, or jointly forms an epoxide group with X; at the 17-position only, or at the 17- and 21-positions when R.sub.5 in formula III is hydroxyl, the said esterification being carried out with the anhydride of the acid containing the group desired.

  这段文字描述了一种制备皮质类固醇酯的过程，其中包括酯化化合物的步骤。
• 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。
• Aromatic heterocyclic esters of steroids, their preparation and pharmaceutical compositions containing them
  申请人：SCHERING CORPORATION

  公开号：EP0057401A1

  公开（公告）日：1982-08-11

  Disclosed herein are novel 3,20-dioxo-1,4-pregnadiene-17-01-17-aromatic heterocyclic carboxylates (and the 6-dehydro and 1,2-dihydro derivatives thereof) of general formula I: wherein: A is hydrogen or, provided that Y is (H,βOH), A may also be chloro, fluoro or methyl; X is hydrogen or a halogen atom having an atomic weight less than 100; Y is oxygen, (H,βOH) or, provided that X is hydrogen, Y may also be (H,H) or, provided X is chloro or bromo, Y may also be (H,β-halogen), the β-halogen having an atomic weight less than 100 and being at least as electronegative as X; Z is hydrogen, methyl, chloro or fluoro; Z' is hydrogen or, provided that Z is hydrogen, may also be halogen having an atomic weight of less than 100; V is an acyl radical of a thiophenecarboxylic acid, pyrrolecarboxylic acid or furancarboxylic acid or the methyl- or halogen-substituted derivatives thereof; W is (H,H), (H, lower alkyl) or (H, aOV,) where V, is hydrogen or specified acyl radicals, or W is a methylene or substituted methylene group; and G is hydrogen, a halogen atom having an atomic weight of less than 100 or is -QV2 where Q is oxygen or sulfur and V2 is specified acyl radicals. The novel compounds exhibit anti-inflammatory activity and their use for this purpose is disclosed. Also disclosed are methods for the preparation of the novel compounds.

  本文公开了通式 I 的新型 3,20-二氧代-1,4-孕二烯-17-01-17-芳香杂环羧酸盐（及其 6-脱氢和 1,2-二氢衍生物）： 其中 A 是氢，或者只要 Y 是（H,βOH），A 也可以是氯、氟或甲基； X 是氢或原子量小于 100 的卤原子； Y 是氧、(H,βOH)，或者，如果 X 是氢，Y 也可以是 (H,H)，或者，如果 X 是氯或溴，Y 也可以是 (H,β-卤素)，β-卤素的原子量小于 100 且至少与 X 具有相同的电负性； Z 是氢、甲基、氯或氟； Z'是氢，如果 Z 是氢，也可以是原子量小于 100 的卤素； V 是噻吩羧酸、吡咯羧酸或呋喃羧酸的酰基或其甲基或卤素取代的衍生物； W 是(H,H)、(H,低级烷基)或(H,aOV,)，其中 V 是氢或特定酰基，或 W 是亚甲基或取代亚甲基；以及 G 是氢、原子量小于 100 的卤原子或-QV2，其中 Q 是氧或硫，V2 是指定的酰基。 这些新型化合物具有抗炎活性，其用途也已公开。此外，还公开了新型化合物的制备方法。
• Steroidal esters and process for the preparation of steroidal esters
  申请人：PLURICHEMIE ANSTALT

  公开号：EP0072200B1

  公开（公告）日：1985-11-21
• US4172132A
  申请人：——

  公开号：US4172132A

  公开（公告）日：1979-10-23