1-Bromo-10-(pentylthio)-decane | 177583-96-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Bromo-10-(pentylthio)-decane
• 英文别名: 1-Bromo-10-pentylsulfanyldecane
• CAS: 177583-96-9
• 化学式: C₁₅H₃₁BrS
• 分子量: 323.381
• InChiKey: CXLAADFTGPKJII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  17
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Bromo-10-(pentylthio)-decane 在 碘 、 sodium hydride 、 magnesium 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E/Z)-(+/-)-3-(4-methoxyphenyl)-4-(3-methoxyphenyl)-14-pentylthiotetradec-2-ene
  参考文献：
  名称：

  基于二苯乙烯的雌酮硫酸酯酶抑制剂在人乳腺癌细胞中具有双重作用

  摘要：

  硫酸雌酮 (E1S) 是一种内源性前药，在被雌酮硫酸酯酶水解后，将雌酮和随后的雌二醇输送到靶细胞，雌酮硫酸酯酶在包括激素依赖性乳腺癌在内的各种组织中都有活性。阻断这种酶会降低乳腺癌细胞中的雌激素水平并防止激素生长刺激。在这项研究中，合成了许多具有保证抗雌激素活性的侧链的氨磺酰氧基取代的芪，并评估了它们作为雌酮硫酸酯酶抑制剂的作用。他们在人 MDA-MB 231 乳腺癌细胞中抑制了这种酶，IC50 值在亚微摩尔范围内。在用雌二醇或硫酸雌酮刺激的转染的 MCF-7/2a 乳腺癌细胞中测定了游离羟基衍生物和氨基磺酸盐对基因激活的影响。数据分析揭示了大多数化合物的双重作用模式。他们通过抑制雌酮硫酸酯酶和抗雌激素作用来阻断基因表达。在抗增殖活性的测定中也观察到这种药理学特征。最有效的衍生物 8g 抑制野生型人 MCF-7 细胞的生长，IC50 值为 13 nM。

  DOI：

  10.1002/ardp.200400904

文献信息

• Synthesis and biological evaluation of stilbene-based pure estrogen antagonists
  作者：Georg Walter、Renate Liebl、Erwin von Angerer

  DOI：10.1016/j.bmcl.2004.06.098

  日期：2004.9

  Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists. (C) 2004 Elsevier Ltd. All rights reserved.
• Antiestrogenic Activities of 3,8-Dihydroxy-6,11-dihydrobenzo[a]carbazoles with Sulfur-Containing Side Chains
  作者：Thomas Golob、Christian Biberger、Georg Walter、Erwin von Angerer

  DOI：10.1002/1521-4184(20009)333:9<305::aid-ardp305>3.0.co;2-q

  日期：2000.9

  The objective of this study was to explore whether the conversion of the 2-phenylindole system into the tetracyclic benzo[a]carbazole changes the endocrine profile when the side chain structure was kept constant. Five different sulfur-containing side chains were linked to the nitrogen of the tetracycle. The biological evaluation revealed that the character of the indole derivatives remained unchanged after the conversion to the respective benzocarbzoles but the potency decreased by one order of magnitude. In vitro, all derivatives acted as pure antiestrogens without any agonist activity. They strongly inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells with IC50-values in the nanomolar range. In the mouse uterine weight test, the derivatives with an aliphatic side chain were devoid of estrogenic activity and antagonized the effect of estradiol. The presence of an aromatic ring in the side chain gave rise to significant agonist activity in vivo independently of the carrier structure. All data revealed the equivalence of both carrier structures in respect to the endocrine profile but showed a decrease in potency upon the conversion of the 2-phenylindole system into the benzocarbazole structure.
• US6147105A
  申请人：——

  公开号：US6147105A

  公开（公告）日：2000-11-14
• US6503938B1
  申请人：——

  公开号：US6503938B1

  公开（公告）日：2003-01-07
• Stilbene-Based Inhibitors of Estrone Sulfatase with a Dual Mode of Action in Human Breast Cancer Cells
  作者：Georg Walter、Renate Liebl、Erwin von Angerer

  DOI：10.1002/ardp.200400904

  日期：2004.12

  evaluated as inhibitors of estrone sulfatase. They inhibited this enzyme in human MDA‐MB 231 breast cancer cells, with IC50 values in the submicromolar range. The effects of both the free hydroxy derivatives and the sulfamates on gene activation were determined in transfected MCF‐7/2a breast cancer cells stimulated either with estradiol or with estrone sulfate. The analysis of data revealed a dual mode of action

  硫酸雌酮 (E1S) 是一种内源性前药，在被雌酮硫酸酯酶水解后，将雌酮和随后的雌二醇输送到靶细胞，雌酮硫酸酯酶在包括激素依赖性乳腺癌在内的各种组织中都有活性。阻断这种酶会降低乳腺癌细胞中的雌激素水平并防止激素生长刺激。在这项研究中，合成了许多具有保证抗雌激素活性的侧链的氨磺酰氧基取代的芪，并评估了它们作为雌酮硫酸酯酶抑制剂的作用。他们在人 MDA-MB 231 乳腺癌细胞中抑制了这种酶，IC50 值在亚微摩尔范围内。在用雌二醇或硫酸雌酮刺激的转染的 MCF-7/2a 乳腺癌细胞中测定了游离羟基衍生物和氨基磺酸盐对基因激活的影响。数据分析揭示了大多数化合物的双重作用模式。他们通过抑制雌酮硫酸酯酶和抗雌激素作用来阻断基因表达。在抗增殖活性的测定中也观察到这种药理学特征。最有效的衍生物 8g 抑制野生型人 MCF-7 细胞的生长，IC50 值为 13 nM。