2-methylsulfanyl estrone 3-O-sulfamate | 401600-84-8

• 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: 2-methylsulfanyl estrone 3-O-sulfamate
• 英文别名: (8R,9S,13S,14S)-13-Methyl-2-methylsulfanyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3-sulfonic acid amide；[(8R,9S,13S,14S)-13-methyl-2-methylsulfanyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] sulfamate
• CAS: 401600-84-8
• 化学式: C₁₉H₂₅NO₄S₂
• 分子量: 395.544
• InChiKey: UAFZHFZPOUPSTQ-QPWUGHHJSA-N

物化性质

• 熔点：
  184-185 °C
• 沸点：
  554.9±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methylsulfanyl estrone 3-O-sulfamate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到Sulfamic acid (8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-2-methylsulfanyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents

  摘要：

  A flexible, direct, high yielding synthesis of 2-alkylsulfanyl estrogens from estrone has been developed. 2-Methylsulfanyl estradiol (2-MeSE2) 7 displays a similar anti-proliferative activity to the established 2-methoxyestradiol (2-MeOE2) 1, whilst its 3-O-sulfamate derivative (2-MeSE2MATE) 9 exhibits greatly enhanced anti-proliferative activity, combined with significant inhibition of steroid sulfatase, an enzyme target for the treatment of hormone-dependent tumours. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.027
• 作为产物：
  描述：

  雌酚酮 在 盐酸 、 氨基磺酰氯 、 仲丁基锂 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 2-methylsulfanyl estrone 3-O-sulfamate
  参考文献：
  名称：

  2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents

  摘要：

  A flexible, direct, high yielding synthesis of 2-alkylsulfanyl estrogens from estrone has been developed. 2-Methylsulfanyl estradiol (2-MeSE2) 7 displays a similar anti-proliferative activity to the established 2-methoxyestradiol (2-MeOE2) 1, whilst its 3-O-sulfamate derivative (2-MeSE2MATE) 9 exhibits greatly enhanced anti-proliferative activity, combined with significant inhibition of steroid sulfatase, an enzyme target for the treatment of hormone-dependent tumours. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.027

文献信息

• Compositions comprising oestrone-3-0-sulphamate and trail (TNF-related apoptosis inducing ligand)
  申请人：——

  公开号：US20040166090A1

  公开（公告）日：2004-08-26

  The present invention provides a composition comprising (i) a compound comprising a sulphamate group (“a sulphamate compound”); and (ii) an apoptosis inducer.

  本发明提供了一种组合物，该组合物包含：(i) 含有氨基磺酸基团的化合物（"氨基磺酸化合物"）；(ii) 细胞凋亡诱导剂。
• A-Ring-Substituted Estrogen-3-<i>O</i>-sulfamates:  Potent Multitargeted Anticancer Agents
  作者：Mathew P. Leese、Hatem A. M. Hejaz、Mary F. Mahon、Simon P. Newman、Atul Purohit、Michael J. Reed、Barry V. L. Potter

  DOI：10.1021/jm050066a

  日期：2005.8.1

  Efficient and flexible syntheses of 2-substituted estrone, estradiol and their 3-O-sulfamate (EMATE) derivatives have been developed using directed ortho-lithiation methodology. 2-Substituted EMATEs display a similar antiproliferative activity profile to the corresponding estradiols against a range of human cancer cell lines. 2-Methoxy (3, 4), 2-methylsulfanyl (20, 21) and 2-ethyl EMATEs (32, 33) proved the most active compounds with 2-ethylestradiol-3-O-sulfamate (33), displaying a mean activity over the NCI 55 cell line panel 80-fold greater than the established anticancer agent 2-methoxyestradiol (2). 2-Ethylestradiol-3-O-sulfamate (33) was also an effective inhibitor of angiogenesis using three in vitro markers, and various 2-substituted EMATEs also proved to be inhibitors of steroid sulfatase (STS), a therapeutic target for the treatment of hormone-dependent breast cancer. The potential of this novel class of multimechanism anticancer agents was confirmed in vivo with good activity observed in the NCI hollow fiber assay and in a MDA-MB-435 xenograft mouse model.
• COMPOSITIONS COMPRISING OESTRONE-3-O-SULPHAMATE AND TRAIL (TNF-RELATED APOPTOSIS INDUCING LIGAND)
  申请人：Sterix Limited

  公开号：EP1399221A1

  公开（公告）日：2004-03-24
• US7211246B2
  申请人：——

  公开号：US7211246B2

  公开（公告）日：2007-05-01
• [EN] COMPOSITIONS COMPRISING OESTRONE-3-0-SULPHAMATE AND TRAIL (TNF-RELATED APOPTOSIS INDUCING LIGAND)<br/>[FR] COMPOSITIONS COMPRENANT DE L'OESTRONE-3-0-SULFAMATE ET DU TRAIL (LIGAND INDUISANT L'APOPTOSE EN RELATION AVEC LE TNF)
  申请人：STERIX LTD

  公开号：WO2002098511A1

  公开（公告）日：2002-12-12

  The present invention provides a composition comprising (i) a compound comprising a sulphamate group ('a sulphamate compound'); and (ii) an apoptosis inducer.