2-ethyl-17-oxoestra-1,3,5(10)-trien-3-yl sulphamate | 304681-51-4

• 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-ethyl-17-oxoestra-1,3,5(10)-trien-3-yl sulphamate
• 英文别名: 2-ethyl-17-oxoestra-1,3,5(10)-trien-3-yl sulfamate；2-methoxyestrone-3-O-sulfamate；2-ethylestrone 3-O-sulphamate；(9beta)-2-Ethyl-17-Oxoestra-1(10),2,4-Trien-3-Yl Sulfamate；[(8R,9S,13S,14S)-2-ethyl-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] sulfamate
• CAS: 304681-51-4
• 化学式: C₂₀H₂₇NO₄S
• 分子量: 377.505
• InChiKey: GTMOGHHWTKSVCD-MQJTVSLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethyl-17-oxoestra-1,3,5(10)-trien-3-yl sulphamate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 3.0h， 以73%的产率得到(14beta,17alpha)-2-Ethyl-17-Hydroxyestra-1(10),2,4-Trien-3-Yl Sulfamate
  参考文献：
  名称：

  A-Ring-Substituted Estrogen-3-O-sulfamates:  Potent Multitargeted Anticancer Agents

  摘要：

  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.

  DOI：

  10.1021/jm050066a
• 作为产物：
  描述：

  雌酮17-乙烯缩酮 在 盐酸 、 氨基磺酰氯 、 仲丁基锂 、 sodium hydride 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 为溶剂， 反应 36.17h， 生成 2-ethyl-17-oxoestra-1,3,5(10)-trien-3-yl sulphamate
  参考文献：
  名称：

  A-Ring-Substituted Estrogen-3-O-sulfamates:  Potent Multitargeted Anticancer Agents

  摘要：

  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.

  DOI：

  10.1021/jm050066a

文献信息

• Methods for treating or preventing cancer by preventing, inhibiting, or arresting cell cycling
  申请人：Reed John Michael

  公开号：US20060122161A1

  公开（公告）日：2006-06-08

  There is provided use of a cyclic compound or a pharmaceutically active salt thereof in the manufacture of a medicament to prevent and/or inhibit and/or arrest cell cycling, wherein the cyclic compound comprises at least one ring, wherein Group I and Group II, independently of each other, are attached to a ring of the cyclic compound; wherein Group I is a hydrocarbyl or an oxyhydrocarbyl group; and wherein Group II is a group of the formula X is P or S; when X is P, Y is ═O or S, Z is —OH and R is hydrocarbyl or H; when X is S, Y is ═O, Z is ═O, and R is hydrocarbyl or N(R 1 )(R 2 ), wherein each of R 1 and R 2 is independently selected from H or a hydrocarbyl group.

  提供使用环状化合物或其药物活性盐制造药物，以预防和/或抑制和/或阻止细胞周期，其中该环状化合物包含至少一个环，其中第I组和第II组独立地附着于环状化合物的一个环上；其中第I组是一个羟基烷基或氧羟基烷基基团；第II组是公式X的基团：X为P或S；当X为P时，Y为═O或S，Z为—OH，R为烃基或H；当X为S时，Y为═O，Z为═O，R为烃基或N（R1）（R2），其中每个R1和R2独立地选择自H或烃基团。
• Thioether sulphamate steroids as steroid inhibtors and anti-cancer compounds
  申请人：——

  公开号：US20040009959A1

  公开（公告）日：2004-01-15

  There is provided use of a compound in the manufacture of a medicament to inhibit superoxide dismutase (SOD) or for use in the therapy of a condition or disease associated with SOD wherein the compound is of Formula I 1 wherein: X is a ring having at least 4 atoms in the ring; K is a hydrocarbyl group; R 1 is a halogen or a group of the formula -L 1 -Z-R 1 , wherein L 1 is an optional linker group, Z is O or S and R 1 is a hydrocarbyl group or H; with the proviso that the compound is other than 2-methoxy-17&bgr;-oestradiol, 2-methoxyoestrone and 2-hydroxyestradiol.

  提供了一种化合物在药物制造中的应用，用于抑制超氧化物歧化酶（SOD）或用于治疗与SOD相关的疾病或病症，其中该化合物的化学式为I1，其中：X是至少有4个原子的环；K是一个烃基；R1是卤素或公式-L1-Z-R1的基团，其中L1是可选的连接基团，Z是O或S，R1是烃基或氢；但该化合物不包括2-甲氧基-17β-雌二醇，2-甲氧基雌酮和2-羟基雌二醇。
• 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。
• USE OF ESTRONE DERIVATIVES AS ANTITUMOUR AGENTS
  申请人：Sterix Limited

  公开号：EP1173182A2

  公开（公告）日：2002-01-23
• 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