3-(2-氯乙基)-1-[(7S)-1,2,3-三甲氧基-10-甲硫基-9-氧代-6,7-二氢-5H-苯并[d]庚搭烯-7-基]脲 | 75776-08-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 中文名称: 3-(2-氯乙基)-1-[(7S)-1,2,3-三甲氧基-10-甲硫基-9-氧代-6,7-二氢-5H-苯并[d]庚搭烯-7-基]脲
• 英文名称: N-deacetyl-N-<(2-chloroethyl)carbamoyl>methylthiocolchicine
• 英文别名: Urea, 1-(2-chloroethyl)-3-(10-methylthio-9-oxo-1,2,3-trimethoxy-5,6,7,9-tetrahydrobenzo(a)heptalen-7-yl)-；1-(2-chloroethyl)-3-(1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)urea
• CAS: 75776-08-8
• 化学式: C₂₃H₂₇ClN₂O₅S
• 分子量: 478.997
• InChiKey: JAWNITNZPHEEQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-氯乙基)-1-[(7S)-1,2,3-三甲氧基-10-甲硫基-9-氧代-6,7-二氢-5H-苯并[d]庚搭烯-7-基]脲 在 溶剂黄146 、 sodium nitrite 作用下， 反应 1.0h， 以68%的产率得到N-deacetyl-N-methylthiocolchicine
  参考文献：
  名称：

  Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine

  摘要：

  A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed.

  DOI：

  10.1021/jm00186a028
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 7-amino-1,2,3-trimethoxy-10-methylsulfanyl-6,7-dihydro-5H-benzo[a]-heptalen-9-one 以 甲醇 、 水 为溶剂， 反应 2.0h， 以52%的产率得到3-(2-氯乙基)-1-[(7S)-1,2,3-三甲氧基-10-甲硫基-9-氧代-6,7-二氢-5H-苯并[d]庚搭烯-7-基]脲
  参考文献：
  名称：

  Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine

  摘要：

  A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed.

  DOI：

  10.1021/jm00186a028

文献信息

• LIN T.; SHIAU G. T.; PRUSOFF W. H.; HARMON R. E., J. MED. CHEM., 1980, 23, NO 12, 1440-1442
  作者：LIN T.、 SHIAU G. T.、 PRUSOFF W. H.、 HARMON R. E.

  DOI：——

  日期：——
• Synthesis and biological activities of chloroethylurea, methylurea, and nitrosourea analogs of N-deacetylmethylthiocolchicine
  作者：Tai-Shun Lin、George T. Shiau、William H. Prusoff、Robert E. Harmon

  DOI：10.1021/jm00186a028

  日期：1980.12

  A series of urea and nitrosourea analogues of N-deacetylmethylthiocolchicine (1) has been synthesized, and their antineoplastic and antiviral activities were evaluated. The objective for combination of two active moieties, such as thiocolchicine and nitrosourea, into one molecule was the generation of compounds with potential improved biological and pharmacological properties. The ED50 for 2, 3, 4, and 5 was 1.6, 1.2, 3.3, and 1.8 X 10(-8) M for L1210 cells and 3.0, 2.7, 2.9, and 2.6 X 10(-8) M for S-180 cells, respectively. The synthesis and cytotoxic and antiviral properties of these compounds are discussed.