(E)-3-(2-chloro-4-fluorophenyl)propenal | 262268-44-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(2-chloro-4-fluorophenyl)propenal
• 英文别名: 3-(2-Chloro-4-fluorophenyl)acrylaldehyde；(E)-3-(2-chloro-4-fluorophenyl)prop-2-enal
• CAS: 262268-44-0
• 化学式: C₉H₆ClFO
• 分子量: 184.597
• InChiKey: QFOGQBURVXYBSQ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-氯-4-氟苯甲醛	2-chloro-4-fluorobenzaldehyde	84194-36-5	C7H4ClFO	158.56

反应信息

• 作为反应物：
  描述：

  (E)-2-[2-(Dimethoxy-phosphorylmethyl)-phenyl]-3-methoxy-acrylic acid methyl ester 、 (E)-3-(2-chloro-4-fluorophenyl)propenal 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 (E)-2-[2-[(1E,3E)-4-(2-chloro-4-fluoro-phenyl)-buta-1,3-dienyl]-phenyl]-3-methoxy-acrylic acid methyl ester
  参考文献：
  名称：

  Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore

  摘要：

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.

  DOI：

  10.1021/jm990002y
• 作为产物：
  描述：

  2-氯-4-氟苯甲醛 在 盐酸 、 sodium methylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.75h， 生成 (E)-3-(2-chloro-4-fluorophenyl)propenal
  参考文献：
  名称：

  Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore

  摘要：

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.

  DOI：

  10.1021/jm990002y

文献信息

• [EN] CARBOLINE ANTIPARASITICS<br/>[FR] ANTIPARASITAIRES À BASE DE CARBOLINE
  申请人：ZOETIS SERVICES LLC

  公开号：WO2016209635A1

  公开（公告）日：2016-12-29

  The present invention provides Formula (1 ) compounds that are gamma-carbolines, Formula (1) wherein R1 a, R1 b, R1 c, R1d, R2, R3, and "— " are as defined herein; veterinary acceptable salts thereof, and stereoisomers thereof, which act as parasiticides, in particular, endoparasiticides.

  本发明提供了一种γ-咔啉化合物的化学式（1），其中R1a，R1b，R1c，R1d，R2，R3和“—”如本文所定义；其兽用可接受盐，以及对映异构体，可作为寄生虫药物，特别是内寄生虫药物。
• Carboline antiparasitics
  申请人：Zoetis Services LLC

  公开号：US10570129B2

  公开（公告）日：2020-02-25

  The present invention provides Formula (1) compounds that are gamma-carbolines, Formula (1) wherein R1a, R1b, R1c, R1d, R2, R3, and “-” are as defined herein; veterinary acceptable salts thereof, and stereoisomers thereof, which act as parasiticides, in particular, endoparasiticides.

  本发明提供了属于γ-羰基化合物的式(1)化合物，式(1)中的R1a、R1b、R1c、R1d、R2、R3和"-"如本文所定义；其兽药可接受盐及其立体异构体，可作为杀寄生虫剂，特别是内吸性杀寄生虫剂。
• CARBOLINE ANTIPARASITICS
  申请人：Zoetis Services LLC

  公开号：EP3313837A1

  公开（公告）日：2018-05-02
• Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore
  作者：Jawad Alzeer、Jacques Chollet、Ingrid Heinze-Krauss、Christian Hubschwerlen、Hugues Matile、Robert G. Ridley

  DOI：10.1021/jm990002y

  日期：2000.2.1

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.