1,3-bis(4-cyanophenyl)-2,3-dibromopropan-1-one | 229308-73-0

• 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: 1,3-bis(4-cyanophenyl)-2,3-dibromopropan-1-one
• 英文别名: 2,3-dibromo-1,3-bis(4-cyanophenyl)propan-1-one；4-[1,2-dibromo-3-(4-cyanophenyl)-3-oxopropyl]benzonitrile
• CAS: 229308-73-0
• 化学式: C₁₇H₁₀Br₂N₂O
• 分子量: 418.087
• InChiKey: CVSRBDSLVKERTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-cyanophenyl)-2,3-dibromopropan-1-one 在 trimethylsulfonium iodide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 10.5h， 生成 2,4-bis(4-cyanophenyl)furan
  参考文献：
  名称：

  2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis carinii Pneumonia Agents

  摘要：

  Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)(2). All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7-10 at the dose of 10 mu mol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 mu mol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity.

  DOI：

  10.1021/jm990071c
• 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， 反应 3.0h， 生成 1,3-bis(4-cyanophenyl)-2,3-dibromopropan-1-one
  参考文献：
  名称：

  2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis carinii Pneumonia Agents

  摘要：

  Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)(2). All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7-10 at the dose of 10 mu mol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 mu mol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity.

  DOI：

  10.1021/jm990071c

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。
• 2,4-bis[(4-amidino)phenyl]furans as anti-Pneumocystis carinii agents
  申请人：The University of North Carolina at Chapel Hill

  公开号：US06127554A1

  公开（公告）日：2000-10-03

  Compounds according to the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are each independently selected from the group consisting of H, loweralkyl, aryl, alkylaryl, aminoalkyl, aminoaryl, halogen, oxyalkyl, oxyaryl, or oxyarylalkyl; R.sub.3 and R.sub.4 are each independently selected from the group consisting of H, loweralkyl, oxyalkyl, alkylaryl, aryl, oxyaryl, aminoalkyl, aminoaryl, or halogen; and X and Y are located in the para or meta positions and are each selected from the group consisting of H, loweralkyl, oxyalkyl, and ##STR2## wherein: each R.sub.5 is independently selected from the group consisting of H, loweralkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, cycloalkyl, aryl, or alkylaryl or two R.sub.5 groups together represent C.sub.2 to C.sub.10 alkyl, hydroxyalkyl, or alkylene; and R.sub.6 is H, hydroxy, loweralkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, alkylamino, lkylaminoalkyl, cycloalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aryl, or alkylaryl; or a pharmaceutically acceptable salt thereof, are disclosed. The compounds are useful for treating Pneumocystis carinii in a subject in need of such treatment.

  化合物的公式为：##STR1##其中：R.sub.1和R.sub.2各自独立地选自以下组：H，低碳基，芳基，烷基芳基，氨基烷基，氨基芳基，卤素，氧烷基，氧芳基或氧芳基烷基；R.sub.3和R.sub.4各自独立地选自以下组：H，低碳基，氧烷基，烷基芳基，芳基，氧芳基，氨基烷基，氨基芳基或卤素；X和Y位于对位或间位，各自选择自以下组：H，低碳基，氧烷基和##STR2##其中：每个R.sub.5独立地选自以下组：H，低碳基，烷氧基烷基，羟基烷基，氨基烷基，烷基氨基烷基，环烷基，芳基或烷基芳基，或两个R.sub.5基团共同代表C.sub.2到C.sub.10的烷基，羟基烷基或烷基烷；R.sub.6是H，羟基，低碳基，烷氧基烷基，羟基烷基，氨基烷基，烷基氨基，烷基氨基烷基，环烷基，羟基环烷基，烷氧基环烷基，芳基或烷基芳基；或其药学上可接受的盐。这些化合物可用于治疗需要此类治疗的主体的卡氏肺孢子虫。
• Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles
  作者：Donald A. Patrick、Stanislav A. Bakunov、Svetlana M. Bakunova、E. V. K. Suresh Kumar、Richard J. Lombardy、Susan Kilgore Jones、Arlene S. Bridges、Oksana Zhirnov、James Edwin Hall、Tanja Wenzler、Reto Brun、Richard R. Tidwell

  DOI：10.1021/jm0612867

  日期：2007.5.1

  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.
• US6008247
  申请人：——

  公开号：——

  公开（公告）日：——
• 2,4-Bis (4-amidino)phenyl furans as anti-pneumocystis carinii agents
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP0941991B1

  公开（公告）日：2001-12-05