N-chlorambucil-D-tyrosinol | 1260612-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-chlorambucil-D-tyrosinol
• 英文别名: N-(chlorambucilyl)-D-p-tyrosinol；4-[4-[bis(2-chloroethyl)amino]phenyl]-N-[(2R)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]butanamide
• CAS: 1260612-31-4
• 化学式: C₂₃H₃₀Cl₂N₂O₃
• 分子量: 453.409
• InChiKey: OHOBQHMUVODGTO-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-chlorambucil-D-tyrosine methyl ester 在 锂硼氢 作用下， 以 乙醚 为溶剂， 生成 N-chlorambucil-D-tyrosinol
  参考文献：
  名称：

  Synthesis of d- and l-tyrosine-chlorambucil analogs active against breast cancer cell lines

  摘要：

  A series of D- and L-tyrosine-chlorambucil analogs was synthesized as anticancer drugs for chemotherapy of breast cancer. The novel compounds were synthesized in good yields through efficient modifications of D-and L-tyrosine. The newly synthesized compounds were evaluated for their anticancer efficacy in different hormone-dependent and hormone-independent (ER+ and ER-) breast cancer cell lines. The novel analogs showed significant in vitro anticancer activity when compared to chlorambucil. Structure-activity relationship (SAR) reveals both, the influence of the length of the spacer chain and the stereochemistry of the tyrosine moiety. Interestingly, the D-and L-tyrosinol-chlorambucil derivatives with 10 carbon atoms spacer are selective towards MCF-7 (ER+) breast cancer cell line. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.039

文献信息

• Synthesis of d- and l-tyrosine-chlorambucil analogs active against breast cancer cell lines
  作者：Caroline Descôteaux、Valérie Leblanc、Kevin Brasseur、Atul Gupta、Éric Asselin、Gervais Bérubé

  DOI：10.1016/j.bmcl.2010.10.039

  日期：2010.12

  A series of D- and L-tyrosine-chlorambucil analogs was synthesized as anticancer drugs for chemotherapy of breast cancer. The novel compounds were synthesized in good yields through efficient modifications of D-and L-tyrosine. The newly synthesized compounds were evaluated for their anticancer efficacy in different hormone-dependent and hormone-independent (ER+ and ER-) breast cancer cell lines. The novel analogs showed significant in vitro anticancer activity when compared to chlorambucil. Structure-activity relationship (SAR) reveals both, the influence of the length of the spacer chain and the stereochemistry of the tyrosine moiety. Interestingly, the D-and L-tyrosinol-chlorambucil derivatives with 10 carbon atoms spacer are selective towards MCF-7 (ER+) breast cancer cell line. (C) 2010 Elsevier Ltd. All rights reserved.