3-chloro-N-(4-pyridyl)benzo<β>thiophene-2-carboxamide | 65469-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-chloro-N-(4-pyridyl)benzo<β>thiophene-2-carboxamide
• 英文别名: 3-chloro-N-(pyridin-4-yl)benzo[b]thiophene-2-carboxamide；3-chloro-N-(4-pyridyl)benzo[b]thiophene-2-carboxamide；3-chloro-benzo[b]thiophene-2-carboxylic acid pyridin-4-ylamide；3-chloro-N-pyridin-4-yl-1-benzothiophene-2-carboxamide
• CAS: 65469-41-2
• 化学式: C₁₄H₉ClN₂OS
• mdl: MFCD01022048
• 分子量: 288.757
• InChiKey: VRCFEDBVJWWFKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  215-220 °C(Solv: methanol (67-56-1))
• 沸点：
  404.2±35.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)
• 溶解度：
  0.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(4-pyridyl)benzo<β>thiophene-2-carboxamide 在 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 苯 为溶剂， 生成 6-chloro<1>benzothieno<2,3-c><1,6>naphthyridine
  参考文献：
  名称：

  Kudo, Hirotaka; Takahashi, Kazufumi; Castle, Raymond N., Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1009 - 1011

  摘要：

  DOI：
• 作为产物：
  描述：

  肉桂酸 在 吡啶 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 氯苯 为溶剂， 反应 2.0h， 生成 3-chloro-N-(4-pyridyl)benzo<β>thiophene-2-carboxamide
  参考文献：
  名称：

  接受开放创新的疟疾药物发现邀请：苯并[ b ]噻吩-2-羧酰胺类抗疟药的合成，生物学评估和结构-活性关系的研究

  摘要：

  消灭疟疾是全球卫生的重中之重，但是当前的治疗方法并不总是适合提供彻底的治疗方法。青蒿素为目前的疟疾治疗铺平了道路，所谓的基于青蒿素的联合疗法（ACT）。但是，随着对ACT的抗性的检测，需要对多种寄生虫物种具有多种生命周期且具有活性的创新化合物。葛兰素史克最近披露了内部图书馆的表型筛选结果，发表了400种抗疟药化学型的集合，称为“疟疾箱”。对数据集进行分析后，我们开展了一项药物化学研究活动，以定义一种释放化合物的结构-活性关系，该关系体现了苯并噻吩-2-羧酰胺核心。制备了35种化合物，本文报道了恶性疟原虫，毒性和代谢稳定性。

  DOI：

  10.1021/acs.jmedchem.6b01685

文献信息

• Novel Derivatives of Pyridylbenzo[<i>b</i>]thiophene-2-carboxamides and Benzo[<i>b</i>]thieno[2,3-<i>c</i>]naphthyridin-2-ones: Minor Structural Variations Provoke Major Differences of Antitumor Action Mechanisms
  作者：Katja Ester、Marijana Hranjec、Ivo Piantanida、Irena Ćaleta、Ivana Jarak、Krešimir Pavelić、Marijeta Kralj、Grace Karminski-Zamola

  DOI：10.1021/jm801573v

  日期：2009.4.23

  Novel cyano- and 2-imidazolinyl-substituted derivatives of pyridylbenzo[b]thiophene-2-carboxamides 4, 5, 10-13 and benzo[b]thieno[2,3-c]naphthyridin-2-ones 6, 7, 14-17 were prepared. All derivatives showed a prominent antiproliferative effect. Extensive DNA binding studies and additional biological evaluations point to various modes/targets of action. The results strongly support intercalation into DNA as a dominant binding mode of fused analogues, which was substantiated using topoisomerase I inhibition assay. Most intriguingly, only minor structural difference between "nonfused" compounds 12 and 13 has strong impact on the interactions with DNA; while 13 binds within the DNA minor groove in the form of dimer, 12 does not form significant interactions with DNA. The assumption that severe mitotic impairment (G2/M phase arrest) induced by 12 could point to tubulin, another important target, was confirmed by its obvious anti-tubulin activity observed in immunofluorescence assay, whereby treated cells showed disruption of microtubule formation comparable to the effect obtained by paclitaxel. a well-known tubulin antagonist chemotherapeutic.
• Terashima,M. et al., Heterocycles, 1977, vol. 8, p. 421 - 426
  作者：Terashima,M. et al.

  DOI：——

  日期：——
• KUDO, HIROTAKA;TAKAHASHI, KAZUFUMI;CASTLE, RAYMOND N.;LEE, MILTON L., J. HETEROCYCL. CHEM., 24,(1987) N 4, 1009-1011
  作者：KUDO, HIROTAKA、TAKAHASHI, KAZUFUMI、CASTLE, RAYMOND N.、LEE, MILTON L.

  DOI：——

  日期：——
• TERASHIMA M.; SEKI K., HETEROCYCLES, 1977, 8, SPEC. ISSUE, 421-426
  作者：TERASHIMA M.、 SEKI K.

  DOI：——

  日期：——
• COMPOUND, ORGANIC ELECTROLUMINESCENT DEVICE, AND DISPLAY DEVICE
  申请人：SK Materials CO., LTD.

  公开号：US20210143337A1

  公开（公告）日：2021-05-13

  Disclosed is a compound applicable to an electron transport layer, an electron transport assisting layer, a light emitting layer (n-type) of an organic electroluminescent device, an organic electroluminescent device in which said compound is used, and an organic EL display device including the organic electroluminescent device. The organic electroluminescent device includes: a first electrode; a second electrode facing the first electrode; and an organic material layer interposed between the first electrode and the second electrode and includes the compound.