3-(3-hydroxy-3-methylbut-1-ynyl)benzonitrile | 766539-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-hydroxy-3-methylbut-1-ynyl)benzonitrile
• 英文别名: 3-(3-Hydroxy-3-methyl-1-butyn-1-yl)benzonitrile
• CAS: 766539-54-2
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: BPQKNCDHLPRKSG-UHFFFAOYSA-N

物化性质

• 沸点：
  326.2±27.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-3-methylbut-1-ynyl)benzonitrile 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 生成 3-乙炔基-苯甲腈
  参考文献：
  名称：

  Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues

  摘要：

  Fifty novel prodrugs and aza-analogues of 3,5-bis(4-amidinophenyl)isoxazole and its derivatives were prepared. Eighteen of the 24 aza-analogues exhibited IC50 values below 25 nM against Trypanosoma brucei rhodesiense or Plasmodium falciparum. Six compounds had antitrypanosomal IC50 values below 10 nM. Twelve analogues showed similar antiplasmodial activities, including three with sub-nanomolar potencies. Forty-four diamidines (including 16 aza-analogues) and the 26 prodrugs were evaluated for efficacy in mice infected with T. b. rhodesiense STIB900. Six diamidines cured 4/4 mice at daily 5 mg/kg intraperitoneal doses for 4 days, giving results far superior to pentamidine and furamidine. One prodrug attained 3/4 cures at daily 25 mg/kg oral doses for 4 days. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.10.050
• 作为产物：
  描述：

  间氨基苯甲腈 在 2,2'-联吡啶 、 三苯基膦双(三氟甲磺酰亚胺)金 、 sodium carbonate 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 3-(3-hydroxy-3-methylbut-1-ynyl)benzonitrile
  参考文献：
  名称：

  配体辅助的金催化与芳重氮盐交叉偶联：无需外部氧化剂的氧化还原金催化

  摘要：

  金催化的C（sp）–C（sp 2）和C（sp 2）–C（sp 2）交叉偶联反应是通过芳基重氮盐作为偶联伙伴完成的。在bpy配体的帮助下，金（I）物质在没有任何外部氧化剂的情况下被重氮氧化为金（III）。用NMR和ESI-MS监测反应为氮的挤出，随后的Au III还原消除提供了有力的证据，这是关键步骤。

  DOI：

  10.1002/anie.201503546

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 of 3-[4-Acyl-2-(1-methoxy-1-methylethyl)morpholin-3-yl]-benzonitriles as Novel Potassium Channel Openers
  作者：Mei-Shan Lin、Ling-Wei Hsin、Chen-Yu Cheng

  DOI：10.1002/jccs.200400024

  日期：2004.2

  We have previously reported a series of 1,9-dioxa-4-aza-phenanthrene-6-carbonitriles, including compounds 2 & 3, as bladder-selective KCO's. As a continuation of our efforts, we have designed 3-[4-acyl-2-(1-methoxy-1-methylethyl)morpholin-3-yl]-benzonitriles as ringopened analogs of compounds 2 & 3. In this report, we describe the efficient construction of the novel 2,3-disubstituted morpholine structure

  钾通道开放剂 (KCO) 已被证明对平滑肌具有有效的松弛活性。组织选择性 KCO 可用于治疗多种疾病，例如高血压、哮喘和尿失禁。我们之前报道了一系列 1,9-dioxa-4-aza-phenanthrene-6-carbonitriles，包括化合物 2 和 3，作为膀胱选择性 KCO。作为我们努力的延续，我们设计了 3-[4-acyl-2-(1-methoxy-1-methylethyl)morpholin-3-yl]-benzonitros 作为化合物 2 和 3 的开环类似物。在本报告中，我们描述了新型 2,3-二取代吗啉结构的有效构建，如化合物 4-7 的合成所示。化合物4-7对大鼠膀胱逼尿肌条的制备显示出有效的和选择性的松弛剂活性。在这个系列中，
• 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.
• US7951827B2
  申请人：——

  公开号：US7951827B2

  公开（公告）日：2011-05-31