4-乙炔-3-甲氧基苯甲腈 | 914105-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-乙炔-3-甲氧基苯甲腈
• 英文名称: 4-ethynyl-3-methoxybenzonitrile
• CAS: 914105-99-0
• 化学式: C₁₀H₇NO
• 分子量: 157.172
• InChiKey: RNXAVSCCJGNNQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-乙炔-3-甲氧基苯甲腈 在 盐酸羟胺 、 potassium tert-butylate 、 三丁基氧化锡 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 288.0h， 生成 3,5-bis[4-(N'-hydroxy)amidino-2-methoxyphenyl]isoxazole
  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：

  4-羟基-3-甲氧基苯甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 4-乙炔-3-甲氧基苯甲腈
  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。
• Synthesis and Antiprotozoal Activity of Cationic 2-Phenylbenzofurans
  作者：Stanislav A. Bakunov、Svetlana M. Bakunova、Tanja Wenzler、Todd Barszcz、Karl A. Werbovetz、Reto Brun、Richard R. Tidwell

  DOI：10.1021/jm800918v

  日期：2008.11.13

  A series of cationically substituted 2-phenylbenzofurans 1- 49 have been synthesized, and their in vitro antiprotozoal properties against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani, as well as cytotoxicity against mammalian cells, have been evaluated. Eight dications exhibited antitrypanosomal activities comparable to that of pentamidine and melarsoprol. Twenty-six

  已经合成了一系列阳离子取代的2-苯基苯并呋喃1-49，并且已经评估了它们对布鲁氏锥虫，恶性疟原虫和多形利什曼原虫的体外抗原生动物特性，以及对哺乳动物细胞的细胞毒性。八种药物显示出的抗锥虫活性与喷他op和美拉莫尔相当。26种化合物比喷他idine具有更高的活性，并且有7种药物显示出比青蒿素对恶性疟原虫的活性更高。五个同类物对多诺尼乳杆菌的活性比喷他idine高。b。在7和/或2'-位引入甲氧基或羟基，得到对T. b具有高度选择性的衍生物。Rhodesiense，恶性疟原虫和L. donovani。14种2-苯基苯并呋喃在锥虫病的急性小鼠模型中表现出出色的体内功效，以4 x 5 mg / kg的剂量治愈了3/4或4/4的动物。以4 x 1 mg / kg施用的二m 1和二（N-异丙基）am 45的药效与美拉莫尔相当，分别提供3/4和2/4的治疗。
• [EN] AMIDINES AND AMIDINE ANALOGS FOR THE TREATMENT OF BACTERIAL INFECTIONS AND POTENTIATION ANTIBIOTICS<br/>[FR] AMIDINES ET ANALOGUES D'AMIDINE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES ET D'ANTIBIOTIQUES DE POTENTIALISATION
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2019241566A1

  公开（公告）日：2019-12-19

  Compounds and methods for the treatment of a bacterial infection or the potentiation of an antibiotic in treating a bacterial infection are described herein.

  本文描述了用于治疗细菌感染或增强抗生素治疗细菌感染的化合物和方法。
• Synthesis and Antiprotozoal Activity of Cationic 1,4-Diphenyl-1<i>H</i>-1,2,3-triazoles
  作者：Stanislav A. Bakunov、Svetlana M. Bakunova、Tanja Wenzler、Maedot Ghebru、Karl A. Werbovetz、Reto Brun、Richard R. Tidwell

  DOI：10.1021/jm901178d

  日期：2010.1.14

  antiplasmodial IC50 value of 0.6 nM. Seven congeners administered at 4 × 5 mg/kg by the intraperitoneal route cured at least three out of four animals in the acute mouse model of African trypanosomiasis. At 4 × 1 mg/kg, diamidine 46 displayed better antitrypanosomal efficacy than melarsoprol, curing all infected mice.

  新型双阳离子三唑1 - 60由相应的二腈通过 Pinner 方法合成，通过铜（I）催化的叠氮化物-炔环加成（CuAAC）制备。的类型和阳离子部分的放置以及在化合物的体外抗原生动物活性影响芳族取代基的性质1 - 60对布氏锥虫罗得西亚，恶性疟原虫，和杜氏利什曼原虫和它们的用于哺乳动物细胞的细胞毒性。八个同源物显示出低于 10 nM 的抗锥虫 IC 50值。39 种药物对恶性疟原虫更有效比喷他脒 (IC 50 = 58 nM)，并且八种类似物的活性高于青蒿素 (IC 50 = 6 nM)。二咪唑啉60表现出0.6 nM 的抗疟原虫IC 50值。在非洲锥虫病急性小鼠模型中，通过腹膜内途径以 4 × 5 mg/kg 给药的七种同源物至少治愈了四只动物中的三只。在 4 × 1 mg/kg 时，二脒46显示出比美拉索罗更好的抗锥虫效果，治愈所有感染的小鼠。
• AMIDINES AND AMIDINE ANALOGS FOR THE TREATMENT OF BACTERIAL INFECTIONS AND POTENTIATION ANTIBIOTICS
  申请人：Georgia State University Research Foundation, Inc.

  公开号：EP3806836A1

  公开（公告）日：2021-04-21