17-α-[4'-ethynyldimethylbenzylamine]-17-β-testosterone | 1344683-15-3

• 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: 17-α-[4'-ethynyldimethylbenzylamine]-17-β-testosterone
• CAS: 1344683-15-3
• 化学式: C₃₀H₃₉NO₂
• 分子量: 445.645
• InChiKey: JMMAIYUATMYPNM-PTLNFTKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  33.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  炔孕酮 、 4-溴-N,N-二甲基苄胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以85%的产率得到17-α-[4'-ethynyldimethylbenzylamine]-17-β-testosterone
  参考文献：
  名称：

  Novel C,N-chelate platinum(II) antitumor complexes bearing a lipophilic ethisterone pendant

  摘要：

  The novel steroidal carrier ligand 17-alpha[4'-ethynyl-dimethylbenzylamine]-17-beta-testosterone (ET-dmba 1) and the steroid - C,N-chelate platinum(II) derivatives [Pt(ET-dmba)Cl(L)] (L = DMSO (2) and PTA (3; PTA = 1,3,5-triaza-7-phosphaadamantane)) have been prepared. Values of IC50 were calculated for the new platinum complexes 2 and 3 against a panel of human tumor cell lines representative of ovarian (A2780 and A2780cisR) and breast cancers (T47D). At 48 h incubation time complexes 2 and 3 show very low resistance factors (RF of <2) against an A2780 cell line which has acquired resistant to cisplatin and were more active than cisplatin (about 4-fold for 3) in T47D (AR+, AR = androgen receptor). Compound 1 retains a moderate degree of relative binding affinity (RBA = 0.94%) for androgen receptors. The cytotoxicity of the non steroidal platinum analogues [Pt(dmba)Cl(L)] (dmba = dimethylbenzylamine; L = DMSO (4) and PTA (5)) has also been studied for comparison purposes. Theoretical calculations at the BP86/def2-TZVP level of theory on complex 3 have been undertaken. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.12.005