1-chloro-4-(p-carbomethoxyphenyl)-2-hexanone | 102152-73-8

• 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
• 英文名称: 1-chloro-4-(p-carbomethoxyphenyl)-2-hexanone
• 英文别名: 1-Chloro-4-p-carbomethoxyphenyl-2-hexanone；methyl 4-(6-chloro-5-oxohexan-3-yl)benzoate
• CAS: 102152-73-8
• 化学式: C₁₄H₁₇ClO₃
• 分子量: 268.74
• InChiKey: AXKUJOHZQSMBCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloro-4-(p-carbomethoxyphenyl)-2-hexanone 在 sodium azide 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以91%的产率得到1-azido-4-(p-carbomethoxyphenyl)-2-hexanone
  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
• 作为产物：
  描述：

  methyl 4-(1-chloro-1-oxopentan-3-yl)benzoate 、 重氮甲烷 生成 1-chloro-4-(p-carbomethoxyphenyl)-2-hexanone
  参考文献：
  名称：

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

  摘要：

  DOI：

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-去氨基蝶呤的对映异构体，以及它们的合成方法，包括d,L和l,L对映异构体。其中，d,L-10-乙基对映异构体对L1210细胞的作用比l,L-10-乙基对映异构体强三倍，而l,L-10-乙基对映异构体的毒性约为d,L-10-乙基对映异构体的一半。
• DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;SIROTNAK, FRANCIS M.
  作者：DEGRAW, JOSEPH I.、CHRISTIE, PAMELA H.、SIROTNAK, FRANCIS M.

  DOI：——

  日期：——
• DIASTEREOMERS OF 10-ALKYL-10-DIAZAMINOPTERINS AND PROCESS FOR PREPARING THE SAME
  申请人：SRI INTERNATIONAL

  公开号：EP0254726A1

  公开（公告）日：1988-02-03
• US4746659A
  申请人：——

  公开号：US4746659A

  公开（公告）日：1988-05-24
• [EN] DIASTEREOMERS OF 10-ALKYL-10-DIAZAMINOPTERINS AND PROCESS FOR PREPARING THE SAME
  申请人：SRI INTERNATIONAL

  公开号：WO1987004161A1

  公开（公告）日：1987-07-16

  (EN) 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.(FR) La présente invention décrit des diastéréomères de 10-alkyle-10-déazaminoptérines ainsi qu'une synthèse permettant leur préparation en tant que d,L. et l,L.-diastéréomères séparés, les d,L-10-éthyle diastéréomères étant trois fois plus efficaces contre les cellules L1210 que les l,L-10-éthyle diastéréomères, et les l,L-10-éthyle diastéréomères étant environ la moitié moins toxiques que les d,L-10-éthyle diastéréomères.