2-(1,2-苯并异噻唑-3-基)乙腈 | 37839-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(1,2-苯并异噻唑-3-基)乙腈
• 英文名称: 2-(1,2-benzisothiazol-3-yl)acetonitrile
• 英文别名: (1,2-benzisothiazol-3-yl)acetonitrile；benzo[d]isothiazol-3-ylacetonitrile；benzo[d]isothiazol-3-yl-acetonitrile；1,2-Benzisothiazol-3-ylacetonitril；2-(1,2-Benzothiazol-3-yl)acetonitrile
• CAS: 37839-44-4
• 化学式: C₉H₆N₂S
• mdl: MFCD01830324
• 分子量: 174.226
• InChiKey: ABFZQFLAPMDSLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,2-苯并异噻唑-3-基)乙腈 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1,2-苯并异噻唑-3-乙酸
  参考文献：
  名称：

  Synthesis and pharmacological properties of benzisothiazole/benzimidazole derivatives with acidic groups

  摘要：

  The synthesis and the pharmacological evaluation of benzisothiazole and benzimidazole tetrazolyl- and carboxyl-derivatives 1-6 are described. Structural modification was aimed at investigating the influence of two isosteric substituents (tetrazolyl- and carboxyl-) on the title benzofused heterocycles. The antiphlogistic, antipyretic and analgesic activities have been investigated in in vivo experimental models. Additional investigations have been performed in vitro to study the antiplatelet and spasmolytic activity of the compounds synthetized. All the compounds produced peripheral analgesic effects, but were less effective in hot plate test. The tetrazole and the carboxylic benzisothiazole derivatives 2 and 3 proved to be the most effective drugs within the series, exhibiting maximal inhibition of writhes with a potency 3-fold higher than that of acetaminophen. Only compound 5 provided indication for a central analgesic activity since it was active in hot plate test although with a low potency. The findings obtained in these in vivo and in vitro studies indicate that these compounds do not share the same mechanism of action of acetaminophen. All of the compounds under study present lower acute toxicity than acetaminophen when orally administered in mice. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0014-827x(02)01219-3
• 作为产物：
  描述：

  2-benzo[d]isothiazol-3-yl-acetamide 在 三氯氧磷 作用下， 生成 2-(1,2-苯并异噻唑-3-基)乙腈
  参考文献：
  名称：

  1,2-苯并异噻唑类。第三部分 3-取代衍生物

  摘要：

  （1,2-苯并噻唑-3-基）氰基乙酸乙酯是两种互变异构体的混合物，在二甲基亚砜中加热时会分解为（1,2-苯并异噻唑-3-基）乙腈（85％）。用乙醇乙醇钠处理（1,2-苯并噻唑-3-基）丙二酸二乙酯得到乙酸乙酯（1,2-苯并噻唑-3-基）乙酸乙酯，连续水解和脱羧得到3-甲基-1,2-苯并噻唑。3-甲基-1，2-苯并噻唑中的甲基具有抗氧化性。尝试用Vilsmeier-Haack将3-甲基-1,2-苯并噻唑与二甲基甲酰胺和磷酰氯进行甲酰化反应，得到N 2-（3-苯并[ b ]噻吩基）-N 1 N 1-二甲基甲am和N 2的混合物-（2-甲酰基-3-苯并[ b ]噻吩基）-N 1 N 1-二甲基甲am。相反，2-甲基苯并噻唑产生（苯并噻唑-2-基）丙二醛或相关的烯胺。

  DOI：

  10.1039/p19720003006

文献信息

• KINASE INHIBITORS
  申请人：PRINCIPIA BIOPHARMA, INC.

  公开号：US20140323464A1

  公开（公告）日：2014-10-30

  Provided herein are kinase inhibiting compounds and methods of using the same.

  提供的是激酶抑制化合物及其使用方法。
• Synthesis and spasmolytic activity of 2-substituted-3-(.OMEGA.-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds.
  作者：SHUNSUKE NARUTO、HIROYUKI MIZUTA、TOYOKICHI YOSHIDA、HITOSHI UNO、KATSUYOSHI KAWASHIMA、TOSHIAKI KADOKAWA、HARUKI NISHIMURA

  DOI：10.1248/cpb.31.2023

  日期：——

  Several analogs of (Z)-2-(1, 2-benzisoxazol-3-yl)-3-[2-(2-piperidinoethoxy) phenyl]-acrylonitrile (1a), such as (Z)-2-(1, 2-benzisothiazol-3-yl)-, (Z)-2-(1H-indol-3-yl)-, (E)-2-(2-thienyl)-and (E)-2-benzoyl-3-(ω-dialkylaminoalkoxyphenyl) acrylonitriles (2-5), were synthesized by means of the Knoevenagel condensation. The descyano analog (6) was prepared by means of the Wittig reaction. Triethylammonium formate reduction of 1 afforded the dihydro analog (7). The spasmolytic activities of these analogs were examined. Among these compounds, (Z)-2-(1, 2-benzisothiazol-3-yl)-3-[2-(2-piperidinoethoxy) phenyl]-acrylonitrile (2a) and (Z)-2-(1, 2-benzisothiazol-3-yl)-3-[2-(2-morpholinoethoxy) phenyl]-acrylonitrile (2b) showed potent antispasmodic activities in vitro and in vivo (in mice).

  合成了几种(Z)-2-(1,2-苯异噻唑-3-基)-3-[2-(2-哌嗪乙氧基)苯基]-丙烯腈(1a)的类似物，如(Z)-2-(1,2-苯异噻唑-3-基)-、(Z)-2-(1H-吲哚-3-基)-、(E)-2-(2-噻吩基)-和(E)-2-苯甲酰基-3-(ω-二烷基氨基醇苯基)丙烯腈(2-5)，这些化合物是通过Knoevenagel缩合法合成的。去氰类似物(6)是通过Wittig反应制备的。将1与三乙基氨基甲酸盐还原得到二氢类似物(7)。对这些类似物的镇痉活性进行了研究。在这些化合物中，(Z)-2-(1,2-苯异噻唑-3-基)-3-[2-(2-哌嗪乙氧基)苯基]-丙烯腈(2a)和(Z)-2-(1,2-苯异噻唑-3-基)-3-[2-(2-吗啉乙氧基)苯基]-丙烯腈(2b)在体外和体内（小鼠）均表现出强效的抗痉挛活性。
• Synthesis and acidic properties of 1,2-benzisothiazolyl-tetrazoles and analogous alkanoic acids
  作者：P. Vicini、E. Fisicaro

  DOI：10.1002/ardp.2503241120

  日期：1991.11

  5‐(1,2‐benzisothiazolyl)‐tetrazoles and of the analogous 1,2‐benzisothiazolylalkanoic acids have been determined by potentiometry in methanol/water and compared with literature data. The acidic properties are discussed for possible LFER and correlation with the biological activity. The physico‐chemical properties of two series are strictly correlated but do not appear to be responsible for the modulation

  报道了一种合成 1,2-苯并异噻唑的一些四唑基衍生物的新方法。一系列 5-（1,2-苯并异噻唑基）-四唑和类似的 1,2-苯并异噻唑基链烷酸的 pKa 值已通过甲醇/水中的电位测定法确定，并与文献数据进行比较。讨论了可能的 LFER 的酸性特性以及与生物活性的相关性。两个系列的物理化学性质严格相关，但似乎不负责调节它们的生物活性。
• 3-(1,2-benzisothiazol- and isoxazol-5-Y1)-2,4(1H,3H)-pyrimidinedione or thione and 3-(1,2-benzisothiazol- and isoxazol-5-y1)-4(3H)-pyrimidinone or thione herbicidal agents
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0908457B1

  公开（公告）日：2002-11-13
• Vicini; Amoretti; Barocelli, Farmaco, Edizione Scientifica, 1986, vol. 41, # 2, p. 111 - 118
  作者：Vicini、Amoretti、Barocelli、et al.

  DOI：——

  日期：——