(4-{[(2-chloroethyl)(nitroso)carbamoyl]amino}cyclohexyl)methyl acetate | 61137-49-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (4-{[(2-chloroethyl)(nitroso)carbamoyl]amino}cyclohexyl)methyl acetate
• CAS: 61137-49-3
• 化学式: C₁₂H₂₀ClN₃O₄
• 分子量: 305.761
• InChiKey: GSUNXHODQPCMLL-XYPYZODXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  88.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  Acetic acid 4-amino-cyclohexylmethyl ester; hydrochloride 在 三乙胺 、 sodium nitrite 作用下， 以 甲酸 为溶剂， 生成 (4-{[(2-chloroethyl)(nitroso)carbamoyl]amino}cyclohexyl)methyl acetate
  参考文献：
  名称：

  Synthesis of analogs of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea for evaluation as anticancer agents

  摘要：

  The superior activity of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis-trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans-3-methylcyclohexyl, cis-2-methyl-1,3-dithian-5-yl, cis- and trans-2-methyl-1,3-dithian-5-yl-tetraoxide, and 1-methylhexyl (open-chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but three analogues effected 50% cure rates at nontoxic doses, the open-chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans-4) isomers were, with one exception, as active as or, in four of the eight examples, somewhat more active than the corresponding axial-equatorial (cis-4) isomers. In this series, four of the five 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2-chloroethyl analogues.

  DOI：

  10.1021/jm00212a019

文献信息

• Synthesis of analogs of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea for evaluation as anticancer agents
  作者：Thomas P. Johnston、George S. McCaleb、Sarah D. Clayton、Jerry L. Frye、Charles A. Krauth、John A. Montgomery

  DOI：10.1021/jm00212a019

  日期：1977.2

  The superior activity of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis-trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans-3-methylcyclohexyl, cis-2-methyl-1,3-dithian-5-yl, cis- and trans-2-methyl-1,3-dithian-5-yl-tetraoxide, and 1-methylhexyl (open-chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but three analogues effected 50% cure rates at nontoxic doses, the open-chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans-4) isomers were, with one exception, as active as or, in four of the eight examples, somewhat more active than the corresponding axial-equatorial (cis-4) isomers. In this series, four of the five 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2-chloroethyl analogues.