11-bromo-N-butyl-N-methylundecanamide | 155142-81-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-bromo-N-butyl-N-methylundecanamide
• 英文别名: N-butyl-N-methyl-11-bromoundecanamide；11-bromo-undecanoic acid n-butyl-methyl-amide
• CAS: 155142-81-7
• 化学式: C₁₆H₃₂BrNO
• 分子量: 334.34
• InChiKey: ZRFPEJFTRMIWQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-bromo-N-butyl-N-methylundecanamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 N-butyl-N-methyl-11-mercaptoundecanamide
  参考文献：
  名称：

  Synthesis and Antiestrogenic Activity of Diaryl Thioether Derivatives

  摘要：

  The reaction of 1,2-diarylethanol and mercapto side chain catalyzed by ZnI2 was used as a key step in the short (three to five steps) and efficient synthesis of 17 diaryl thioether derivatives. Several of these compounds contain a methyl butyl amide chain and an hydroxyaryl moiety, respectively, for antiestrogenic activity and binding affinity on estrogen receptor. No binding affinity for crude cytosolic preparation of the estrogen receptor was observed for compounds without phenolic group, while a low affinity (0.01-0.05%) was measured for mono- or diphenol derivatives. Like the pure steroidal antiestrogen EM-139, these novel nonsteroidal compounds did not exert any stimulatory effect on cell proliferation of (ER(+)) ZR-75-1 human breast cancer cells and partially reversed the amplitude of the stimulatory effect induced by estradiol on this (ER(+)) cell line. No proliferative or antiproliferative effect on (ER(-)) MDA-MB-231 human breast cancer cells was also observed for three of these compounds (39-41). Among the newly synthesized nonsteroidal compounds, the thioether derivative 41 (N-butyl-N-methyl-13,14-bis(4'-hydroxyphenyl)-12-thiatetradecanamide), with a long methylbutylalkanamide side chain and a diphenolic nucleus, was selected as the best antiestrogenic compound. However;this compound was 100-fold less antiestrogenic in (ER(+)) ZR-75-1 cells than the steroidal antiestrogen EM-139.

  DOI：

  10.1021/jm00034a009
• 作为产物：
  描述：

  11-溴十一酸 在 三正丁胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 生成 11-bromo-N-butyl-N-methylundecanamide
  参考文献：
  名称：

  Synthesis and Antiestrogenic Activity of Diaryl Thioether Derivatives

  摘要：

  The reaction of 1,2-diarylethanol and mercapto side chain catalyzed by ZnI2 was used as a key step in the short (three to five steps) and efficient synthesis of 17 diaryl thioether derivatives. Several of these compounds contain a methyl butyl amide chain and an hydroxyaryl moiety, respectively, for antiestrogenic activity and binding affinity on estrogen receptor. No binding affinity for crude cytosolic preparation of the estrogen receptor was observed for compounds without phenolic group, while a low affinity (0.01-0.05%) was measured for mono- or diphenol derivatives. Like the pure steroidal antiestrogen EM-139, these novel nonsteroidal compounds did not exert any stimulatory effect on cell proliferation of (ER(+)) ZR-75-1 human breast cancer cells and partially reversed the amplitude of the stimulatory effect induced by estradiol on this (ER(+)) cell line. No proliferative or antiproliferative effect on (ER(-)) MDA-MB-231 human breast cancer cells was also observed for three of these compounds (39-41). Among the newly synthesized nonsteroidal compounds, the thioether derivative 41 (N-butyl-N-methyl-13,14-bis(4'-hydroxyphenyl)-12-thiatetradecanamide), with a long methylbutylalkanamide side chain and a diphenolic nucleus, was selected as the best antiestrogenic compound. However;this compound was 100-fold less antiestrogenic in (ER(+)) ZR-75-1 cells than the steroidal antiestrogen EM-139.

  DOI：

  10.1021/jm00034a009

文献信息

• Synthesis and Estrogenic Activity Screening of Some 6,9-Disubstituted Estradiol Derivatives
  作者：Marija N. Sakač、Katarina M. Penov Gaši、Mirjana Popsavin、Evgenija A. Djurendić、Silvana Andrić、Radmila M. Kovačević

  DOI：10.1135/cccc20050479

  日期：——

  Oxidation of estradiol dipropionate (1) with chromium(VI) oxide-3,5-dimethylpyrazole complex yielded 9α-hydroxy-6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate (2) and 6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate (3). Dehydration of compound 2 with phosphorus(V) oxide or acetic anhydride gave 6-oxoestra-1,3,5(10),9(11)-tetraene-3,17β-diyl dipropionate (5). Reduction of compounds 2 and 5 with sodium borohydride afforded 3,6β,9α-trihydroxyestra-1,3,5(10)-triene-17β-yl propionate (4) and 3,6β-dihydroxyestra-1,3,5(10),9(11)-tetraene-17β-yl propionate (6), respectively. The action of thionyl chloride on compound 2 yielded 6-hydroxyestra-1,3,5(10),6,8-pentaene-3,17β-diyl dipropionate (7). Biological tests in vivo of these compounds showed a moderate antiestrogenic activity of compound 4.

  雌二醇二丙酸酯（1）在铬（VI）氧化物-3,5-二甲基吡唑配合物的作用下生成了9α-羟基-6-氧基雌甾-1,3,5（10）-三烯-3,17β-二丙酸二丙酸酯（2）和6-氧基雌甾-1,3,5（10）-三烯-3,17β-二丙酸二丙酸酯（3）。化合物2经过磷（V）氧化物或乙酸酐的脱水反应得到了6-氧基雌甾-1,3,5（10），9（11）-四烯-3,17β-二丙酸二丙酸酯（5）。化合物2和5经过硼氢化钠还原分别得到了3,6β,9α-三羟基雌甾-1,3,5（10）-三烯-17β-基丙酸酯（4）和3,6β-二羟基雌甾-1,3,5（10），9（11）-四烯-17β-基丙酸酯（6）。硫酰氯对化合物2的作用产生了6-羟基雌甾-1,3,5（10），6,8-五烯-3,17β-二丙酸二丙酸酯（7）。这些化合物的体内生物学测试显示化合物4具有中等的抗雌激素活性。
• A Dehydrohalogenation Methodology for Synthesizing Terminal Olefins under Mild Conditions
  作者：Donald Poirier、Marie Bérubé、Fatima Kamal、Jenny Roy

  DOI：10.1055/s-2006-950204

  日期：——

  A new methodology for preparing terminal olefins in good yield by dehydrohalogenation of primary alkyl iodide with tetrabutylammonium fluoride in dimethyl sulfoxide at room temperature is presented. Optimization of the mild reaction conditions and assays on various alkyl iodides are described.

  提出了一种在室温下使用四丁基氟化铵在二甲基亚砜中通过脱卤化氢反应制备高产率末端烯烃的新方法，该方法涉及初级烷基碘化物。描述了温和反应条件的优化以及对各种烷基碘化物的试验。
• Steroids for cancer treatment
  申请人：Pettersson Lars

  公开号：US20070142345A1

  公开（公告）日：2007-06-21

  The present invention relates to novel compounds which are 7α-substituted 17-alkylene-16α-hydroxy steroidal estrogens. This invention specifically relates to estrogen derivatives which contain 7α-substituents and which exhibit anti-estrogenic properties. The present invention also relates to use of said compounds as a medicament, and for the treatment of estrogen dependent disorders, a pharmaceutical composition comprising one or more of said compounds and a method of treatment.

  本发明涉及一种新型化合物，即7α-取代的17-烷基-16α-羟基类固醇雌激素酯化物。本发明特别涉及含有7α-取代基的雌激素衍生物，其具有抗雌激素性能。本发明还涉及上述化合物作为药物的用途，用于治疗雌激素依赖性疾病，包括含有一种或多种上述化合物的制药组合物和治疗方法。
• AN EXPEDITIOUS ROUTE TO 7α-SUBSTITUTED ESTRADIOL DERIVATIVES
  作者：Rosanna Tedesco、John A Katzenellenbogen、Elio Napolitano

  DOI：10.1016/s0040-4039(97)10180-0

  日期：1997.11

  6-Ketoestradiol derivatives are converted in 7 alpha-alkyl substituted estradiol derivatives selectively by alkylation of the generated enolate followed by deoxygenation-deprotection with BF3 . Et2O/Et3SiH. (C) 1997 Elsevier Science Ltd.
• [EN] 17-METHYLENE-OR 17 - SPIRO - CYCLOPROPANE 7 - SUBSTITUTED ESTRA - 1, 3, 5 (10) - TRIENE DERIVATIVES WITH ANTI - ESTROGENIC ACTIVITY<br/>[FR] STEROIDES DESTINES AU TRAITEMENT DU CANCER
  申请人：INNOVENTUS PROJECT AB

  公开号：WO2005077968A3

  公开（公告）日：2006-08-31