(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane | 946132-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane
• 英文别名: (8S,20R)-de-A,B-8-benzoyloxy-20-[(4S)-hydroxy-pent-(1E)-en-yl]pregnane；(8S,20R)-des-A,B-8-benzoyloxy-20-[(4S)-hydroxy-pent-(1E)-enyl]pregnane；[(1R,3aR,4S,7aR)-1-[(E,2R,6S)-6-hydroxyhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 946132-14-5
• 化学式: C₂₄H₃₄O₃
• 分子量: 370.532
• InChiKey: YXSVMGOGJXOSAQ-AAWPXHQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane 在 palladium 10% on activated carbon 2,6-二甲基吡啶 、 乙醇 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (8S,20R)-des-A,B-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnan-8-ol
  参考文献：
  名称：

  2alpha-Methyl and 2beta-Methyl Analogs of 19,26-Dinor-1alpha,25-Dihydroxyvitamin D3 and Their Uses

  摘要：

  这项发明揭示了19,26-去甲基-1α,25-二羟基维生素D3的2α-甲基和2β-甲基类似物以及其药用。这些化合物在体外表现出生物活性，可作为抗癌剂以及治疗银屑病等皮肤疾病，以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的用途。这些化合物在体内几乎没有钙调节活性，因此可用于治疗人类的自身免疫性疾病，以及继发性甲状旁腺功能亢进和肾性骨病。

  公开号：

  US20120283228A1
• 作为产物：
  描述：

  维生素D2 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 pyridine-SO3 complex 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 50.83h， 生成 (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane
  参考文献：
  名称：

  2-Methylene-(20R,25S)-19,27-Dinor-(22E)-Vitamin D Analogs

  摘要：

  本发明披露了2-亚甲基-(20R,25S)-19,27-二去氢-(22E)-维生素D类似物，具体包括2-亚甲基-(20R,25S)-19,27-二去氢-(22E)-1α,25-二羟基维生素D3，以及其药物用途。该化合物表现出显著的活性，可阻止未分化细胞的增殖并诱导它们分化为单核细胞，因此可作为抗癌剂和治疗皮肤病例如银屑病以及皮肤状况如皱纹、松弛肌肤、干燥肌肤和皮脂分泌不足的用途。该化合物也几乎没有钙代谢活性，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨营养不良。该化合物还可用于肥胖症的治疗或预防。

  公开号：

  US20080081800A1

文献信息

• VITAMIN D ANALOG - NEL, METHODS AND USES THEREOF
  申请人：DELUCA Hector F.

  公开号：US20070191316A1

  公开（公告）日：2007-08-16

  Compounds of formula IA or IB are provided where X 1 , X 2 and X 3 are independently selected from H or hydroxy protecting groups and R 1 is selected from straight or branched chain alkyl groups having from 1 to 8 carbon atoms; straight or branched chain alkenyl groups having from 2 to 8 carbon atoms; straight or branched chain hydroxy-substituted alkyl groups having from 1 to 8 carbon atoms; straight and branched chain hydroxy-substituted alkenyl groups having from 2 to 8 carbon atoms. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

  提供了公式为IA或IB的化合物，其中X1、X2和X3独立地选自H或羟基保护基团，R1选自直链或支链烷基，其碳原子数为1至8；直链或支链烯基，其碳原子数为2至8；直链或支链羟基取代的烷基，其碳原子数为1至8；直链和支链羟基取代的烯基，其碳原子数为2至8。这些化合物用于制备药物组合物，并且在治疗各种生物条件方面非常有用。
• Removal of the 26-Methyl Group from 19-nor-1α,25-Dihydroxyvitamin D₃ Markedly Reduces in Vivo Calcemic Activity without Altering in Vitro VDR Binding, HL-60 Cell Differentiation, and Transcription
  作者：Pawel Grzywacz、Grazia Chiellini、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1021/jm1010447

  日期：2010.12.23

  Twelve new analogues of 19-nor-1 alpha,25-dihydroxyvitamin D-3 (5-16) were prepared by convergent syntheses, employing the Wittig-Horner reaction. The necessary Grundmann type ketones (45-48), possessing fixed configurations of the hydroxyl group at C-25, were obtained by a multistep procedure from commercial vitamin D-2 and enantiomers of 1,3-butanediol (23 and 24). We have examined the influence of removal of one of the methyl groups located at C-25 on the biological in vitro and in vivo activity. The in vivo tests showed that the synthesized vitamin D compounds (5-16) exhibit reduced calcemic activity both in bone and in the intestine. However, in vitro potency of 2-methylene and 2 alpha-methyl compounds (5-10, 13, and 14) remained similar or enhanced as compared to that of 1 alpha,25-(OH)(2)D-3.
• 26-Desmethyl-2-methylene-22-ene-19-nor-1α,25-dihydroxyvitamin D3 compounds selectively active on intestine
  作者：Grazia Chiellini、Pawel Grzywacz、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1016/j.steroids.2014.01.012

  日期：2014.5

  Six new analogs of 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3, 6-7 and 8a,b-9a,b, have been synthesized. All compounds are characterized by a trans double bond located in the side chain between C-22 and C-23. While compounds 6 and 7 possess C-26 and C-27 methyls, compounds 8a,b and 9a,b lack one of these groups. A Lythgoe-based synthesis, employing the Wittig-Horner reaction was used for these preparations. Two different types of Delta E-22-25-hydroxy Grundmann's ketone, having either only one stereogenic center located at position C-20 (20 and 21), or two stereogenic centers located at 20- and 25-positions (24a,b-25a,b) were obtained by a multi-step procedure from commercial vitamin D-2. The introduction of a double bond at C-22 appeared to lower biological activity in vitro and in vivo. Further removal of a 26-methyl in these analogs had little effect on receptor binding, HL-60 differentiation and CYP24A expression but markedly diminished or eliminated in vivo activity on bone calcium mobilization while retaining activity on intestinal calcium transport. (C) 2014 Elsevier Inc. All rights reserved.
• VITAMIN D ANALOG: NEL, METHODS AND USES THEREOF
  申请人：Wisconsin Alumni Research Foundation

  公开号：EP1981843B1

  公开（公告）日：2009-12-09
• US7528122B2
  申请人：——

  公开号：US7528122B2

  公开（公告）日：2009-05-05