4-(对羧基苯基)-1-己烯 | 102152-67-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 4-(对羧基苯基)-1-己烯
• 英文名称: 4-(p-carboxyphenyl)-1-hexene
• 英文别名: 4-p-carboxyphenyl-1-hexene；4-Hex-5-en-3-ylbenzoic acid
• CAS: 102152-67-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: IBZMAZDZOLVXFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(对羧基苯基)-1-己烯 、 甲醇 生成 Methyl 4-hex-5-en-3-ylbenzoate
  参考文献：
  名称：

  DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;SIROTNAK, FRANCIS M.

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 4-hex-5-en-3-ylbenzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4-(对羧基苯基)-1-己烯
  参考文献：
  名称：

  Synthesis and biological activity of resolved carbon-10 diastereomers of 10-methyl- and 10-ethyl-10-deazaminopterin

  摘要：

  Synthesis and evaluation of the antitumor drugs 10-methyl- and 10-ethyl-10-deazaminopterin (15a,b) were previously reported for the diastereomeric mixtures, lacking resolution at the C-10 position. In order to assess biological properties of the individual diastereomers, the C-10 isomers of 4-amino-4-deoxy-10-methyl- and 10-ethyl-10-deazapteroic acids (13a,b) were prepared by total synthesis. Coupling with L-glutamate afforded the appropriate diastereomers of the title compounds. Biochemical, transport, and cell growth inhibitory properties in L1210 cells and folate-dependent bacteria were measured. Differences were generally less than 2-fold between diastereomeric pairs, but a factor of 3 was noted for d,L-15b vs. l,L-15b in inhibition of DHFR from L1210 cells and in cytotoxicity toward L1210 cells. An in vivo comparison of the isomers of 15b with racemic compound against L1210 in mice did not show a significant efficacy difference (ILS) among the compounds. However, d,L-15b showed an acute toxicity about 2.5 times that of l,L-15b.

  DOI：

  10.1021/jm00156a026

文献信息

• Diastereomers of 10-alkyl-10-deazaminopterins and process for preparing
  申请人：SRI International

  公开号：US04746659A1

  公开（公告）日：1988-05-24

  Diastereomers of 10-alkyl-10-deazaminopterins are provided, as well as a synthesis for their preparation as the individual d,L. and l,L.-diastereomers, the d,L-10-ethyl diastereomer being three times as potent against L1210 cells as the l,L-10-ethyl diastereomer, and the l,L-10-ethyl diastereomer being approximately one-half as toxic as the d,L-10-ethyl diastereomer.

  提供了10-烷基-10-去氨基对氨基甲酸的非对映体，以及它们的合成方法，作为个别的d,L. 和l,L.-非对映体。其中，d,L-10-乙基非对映体对L1210细胞的作用比l,L-10-乙基非对映体强三倍，而l,L-10-乙基非对映体的毒性大约是d,L-10-乙基非对映体的一半。
• DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;SIROTNAK, FRANCIS M.
  作者：DEGRAW, JOSEPH I.、CHRISTIE, PAMELA H.、SIROTNAK, FRANCIS M.

  DOI：——

  日期：——
• US4746659A
  申请人：——

  公开号：US4746659A

  公开（公告）日：1988-05-24
• Synthesis and biological activity of resolved carbon-10 diastereomers of 10-methyl- and 10-ethyl-10-deazaminopterin
  作者：J. I. DeGraw、P. H. Christie、H. Tagawa、R. L. Kisliuk、Y. Gaumont、F. A. Schmid、F. M. Sirotnak

  DOI：10.1021/jm00156a026

  日期：1986.6

  Synthesis and evaluation of the antitumor drugs 10-methyl- and 10-ethyl-10-deazaminopterin (15a,b) were previously reported for the diastereomeric mixtures, lacking resolution at the C-10 position. In order to assess biological properties of the individual diastereomers, the C-10 isomers of 4-amino-4-deoxy-10-methyl- and 10-ethyl-10-deazapteroic acids (13a,b) were prepared by total synthesis. Coupling with L-glutamate afforded the appropriate diastereomers of the title compounds. Biochemical, transport, and cell growth inhibitory properties in L1210 cells and folate-dependent bacteria were measured. Differences were generally less than 2-fold between diastereomeric pairs, but a factor of 3 was noted for d,L-15b vs. l,L-15b in inhibition of DHFR from L1210 cells and in cytotoxicity toward L1210 cells. An in vivo comparison of the isomers of 15b with racemic compound against L1210 in mice did not show a significant efficacy difference (ILS) among the compounds. However, d,L-15b showed an acute toxicity about 2.5 times that of l,L-15b.