2,3-dibromo-3-(4-cyano-2-methoxyphenyl)-1-(4-cyanophenyl)propan-1-one | 914105-73-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,3-dibromo-3-(4-cyano-2-methoxyphenyl)-1-(4-cyanophenyl)propan-1-one
• 英文别名: 4-[1,2-Dibromo-3-(4-cyanophenyl)-3-oxopropyl]-3-methoxybenzonitrile
• CAS: 914105-73-0
• 化学式: C₁₈H₁₂Br₂N₂O₂
• 分子量: 448.113
• InChiKey: FLKCVPHSIUJFHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dibromo-3-(4-cyano-2-methoxyphenyl)-1-(4-cyanophenyl)propan-1-one 在 盐酸 、 盐酸羟胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 生成 4-[3-(4-Carbamimidoylphenyl)-1,2-oxazol-5-yl]-3-methoxybenzenecarboximidamide
  参考文献：
  名称：

  Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

  摘要：

  3,5-Bis(4-amidinophenyl)isoxazole (3)an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazoleand 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43 were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.

  DOI：

  10.1021/jm0612867
• 作为产物：
  描述：

  对氰基苯乙酮 在 sodium hydroxide 、 溴 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 2,3-dibromo-3-(4-cyano-2-methoxyphenyl)-1-(4-cyanophenyl)propan-1-one
  参考文献：
  名称：

  Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

  摘要：

  3,5-Bis(4-amidinophenyl)isoxazole (3)an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazoleand 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43 were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.

  DOI：

  10.1021/jm0612867

文献信息

• Synthesis and antiprotozoal activity of dicationic 3,5-diphenylisoxazoles
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1719767A1

  公开（公告）日：2006-11-08

  Novel dicationic 3,5-diphenylisoxazole compounds are described. Synthetic routes to these novel compounds are provided. Several of the compounds displayed in vitro activity versus Trypanosoma brucei brucei and Plasmodium falciparum comparable to that of furamidine. A majority of the novel compounds also were less toxic to VERO cells than furamidine.

  描述了一种新型的双阳离子3,5-二苯基异噁唑化合物。提供了合成这些新型化合物的途径。其中几种化合物在体外显示出对布鲁氏锥虫和疟原虫的活性，与呋胺啶相当。大多数新型化合物对VERO细胞的毒性也比呋胺啶小。
• US7951827B2
  申请人：——

  公开号：US7951827B2

  公开（公告）日：2011-05-31