methyl 8-(2,6-dichloro-4-fluorophenoxy)-3,7-dimethyl-2,4,6-octatrienoate | 538315-13-8

• 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: methyl 8-(2,6-dichloro-4-fluorophenoxy)-3,7-dimethyl-2,4,6-octatrienoate
• 英文别名: methyl (2E,4E,6E)-8-(2,6-dichloro-4-fluorophenoxy)-3,7-dimethylocta-2,4,6-trienoate
• CAS: 538315-13-8
• 化学式: C₁₇H₁₇Cl₂FO₃
• 分子量: 359.225
• InChiKey: PKIQBCJUHRLTKF-DERBOZJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 8-(2,6-dichloro-4-fluorophenoxy)-3,7-dimethyl-2,4,6-octatrienoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.5h， 生成 (2E,4E,6E)-8-(2,6-Dichloro-4-fluoro-phenoxy)-3,7-dimethyl-octa-2,4,6-trienoic acid
  参考文献：
  名称：

  Inhibition of Papilloma Formation by Analogues of 7,8-Dihydroretinoic Acid

  摘要：

  The design of analogues of 7,8-dihydroretinoic acid (7,8-dihydro-RA) was based on reported biological activities of this retinoid and its dihydro-TMMP1 analogue and on structural hypotheses. 7-Oxa-7,8-dihydroretinoids (5, 6) were prepared by O-alkylation of phenoxides by methyl 8-bromo-3,7-dimethyl-2,4,6-octatrienoate. In some cases, C-alkylation also occurred. 7-Aza-8-oxo-7,8-dihydroretinoids (12, 13) were synthesized from benzeneamines and the acyl cyano or bromo derivative of the monomethyl ester of 3,7-dimethyl-2,4,6-octatriene-1,8-dioic acid. These monomethyl ester precursors were synthesized from the known analogous aldehyde via an O-trimethylsilyl cyanohydrin. 7-(2,3,5-Trimethylphenoxy)-3,5-dimethyl-2,4,6-octatrienoic acid (6b) was the most active of the 7-oxa-7,8-dihydro-RAs in inhibiting DMBA-initiated and TPA-promoted mouse-skin papillomas. The ED50 was about 4-fold that of etretinate. Two additional 7-oxa-7,8-dihydro-RAs exhibited modest activity in the papilloma assay. Some of the 7-oxa-7,8-dihydro-RAs bind to CRABP and RARalpha.

  DOI：

  10.1021/jm020324t
• 作为产物：
  描述：

  methyl 8-hydroxy-3,7-dimethyl-2,4,6-octatrienoate 在 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 methyl 8-(2,6-dichloro-4-fluorophenoxy)-3,7-dimethyl-2,4,6-octatrienoate
  参考文献：
  名称：

  Inhibition of Papilloma Formation by Analogues of 7,8-Dihydroretinoic Acid

  摘要：

  The design of analogues of 7,8-dihydroretinoic acid (7,8-dihydro-RA) was based on reported biological activities of this retinoid and its dihydro-TMMP1 analogue and on structural hypotheses. 7-Oxa-7,8-dihydroretinoids (5, 6) were prepared by O-alkylation of phenoxides by methyl 8-bromo-3,7-dimethyl-2,4,6-octatrienoate. In some cases, C-alkylation also occurred. 7-Aza-8-oxo-7,8-dihydroretinoids (12, 13) were synthesized from benzeneamines and the acyl cyano or bromo derivative of the monomethyl ester of 3,7-dimethyl-2,4,6-octatriene-1,8-dioic acid. These monomethyl ester precursors were synthesized from the known analogous aldehyde via an O-trimethylsilyl cyanohydrin. 7-(2,3,5-Trimethylphenoxy)-3,5-dimethyl-2,4,6-octatrienoic acid (6b) was the most active of the 7-oxa-7,8-dihydro-RAs in inhibiting DMBA-initiated and TPA-promoted mouse-skin papillomas. The ED50 was about 4-fold that of etretinate. Two additional 7-oxa-7,8-dihydro-RAs exhibited modest activity in the papilloma assay. Some of the 7-oxa-7,8-dihydro-RAs bind to CRABP and RARalpha.

  DOI：

  10.1021/jm020324t

文献信息

• Inhibition of Papilloma Formation by Analogues of 7,8-Dihydroretinoic Acid
  作者：Y. Fulmer Shealy、James M. Riordan、Jerry L. Frye、Linda Simpson-Herren、Brahma P. Sani、Donald L. Hill

  DOI：10.1021/jm020324t

  日期：2003.5.1

  The design of analogues of 7,8-dihydroretinoic acid (7,8-dihydro-RA) was based on reported biological activities of this retinoid and its dihydro-TMMP1 analogue and on structural hypotheses. 7-Oxa-7,8-dihydroretinoids (5, 6) were prepared by O-alkylation of phenoxides by methyl 8-bromo-3,7-dimethyl-2,4,6-octatrienoate. In some cases, C-alkylation also occurred. 7-Aza-8-oxo-7,8-dihydroretinoids (12, 13) were synthesized from benzeneamines and the acyl cyano or bromo derivative of the monomethyl ester of 3,7-dimethyl-2,4,6-octatriene-1,8-dioic acid. These monomethyl ester precursors were synthesized from the known analogous aldehyde via an O-trimethylsilyl cyanohydrin. 7-(2,3,5-Trimethylphenoxy)-3,5-dimethyl-2,4,6-octatrienoic acid (6b) was the most active of the 7-oxa-7,8-dihydro-RAs in inhibiting DMBA-initiated and TPA-promoted mouse-skin papillomas. The ED50 was about 4-fold that of etretinate. Two additional 7-oxa-7,8-dihydro-RAs exhibited modest activity in the papilloma assay. Some of the 7-oxa-7,8-dihydro-RAs bind to CRABP and RARalpha.