(Z)-2-(2-chlorobenzylidene)indolin-3-one | 38073-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-2-(2-chlorobenzylidene)indolin-3-one
• 英文别名: (Z)-2-(2'-chlorobenzylidene)-1,2-dihydroindol-3-one；2-(2-Chlorphenyl)-methylidenindolin-3-on；(2Z)-2-[(2-chlorophenyl)methylidene]-1H-indol-3-one
• CAS: 38073-43-7
• 化学式: C₁₅H₁₀ClNO
• 分子量: 255.703
• InChiKey: OYNPKJICPKNMBR-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2-chlorobenzylidene)indolin-3-one 在 sodium ethanolate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 [1-Benzyl-3-oxo-1,3-dihydro-indol-(2E)-ylidene]-(2-chloro-phenyl)-acetonitrile
  参考文献：
  名称：

  Novel Pyridazino[4,3-b]indoles with Dual Inhibitory Activity against Mycobacterium tuberculosis and Monoamine Oxidase

  摘要：

  Tuberculosis is one of the most common infectious diseases known to man. About 37% of the world's population (about 1.86 billion people) are infected with Mycobacterium tuberculosis. According to the World Health Organization, every year approximately 8 million people develop active tuberculosis and almost 2 million of those die from the disease. The incidence of multidrug-resistant tuberculosis (MDR-TB) is increasing. The present drug regimen for treating tuberculosis has been in existence for 30 years. New drugs that will shorten total treatment duration, improve the treatment of MDR-TB, and address latent tuberculosis are the most urgent need of tuberculosis control programs. A new series of synthetic 3-amino-4-arylpyridazino[4,3-b]indoles (pyridazinoindoles) were identified as inhibitors of Mycobacterium tuberculosis. The design, synthesis, and antimycobacterial activity of these compounds are described. While the most active compounds are still not comparable to the front-line drugs rifampicin and isoniazid, they do show promise. Most of the pyridazinoindoles with appreciable antituberculosis activity also inhibit monoamine oxidase, suggestive of a novel inhibitory effect on mycobacterial redox reactions.

  DOI：

  10.1021/jm030479g
• 作为产物：
  描述：

  邻氨基苯乙酮 在 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (Z)-2-(2-chlorobenzylidene)indolin-3-one
  参考文献：
  名称：

  寻求小分子作为有效的非竞争性流感抑制剂

  摘要：

  一系列支架，即 aurones、3-indolinones、4-quinolones 和肉桂酸-哌嗪杂化物，被设计、合成并在体外针对 A/H1N1pdm09 病毒进行了研究。与分子对接研究中的唾液酸和奥司他韦不同，设计的分子采用不同的结合方式，即在神经氨酸酶的430-cavity中。所有分子都降低了病毒滴度并表现出非细胞毒性以及对 MDCK 细胞的冷冻保护特性。分子 ( Z )-2-(3'-Chloro-benzylidene)-1,2-dihydro-indol-3-one ( 2f ), ( Z )-2-(4'-Chloro-benzylidene)-1,2- dihydro-indol-3-one ( 2g ) 和 2-(2'-Methoxy-phenyl)-1H-quinolin-4-one ( 3a) 是本研究中鉴定出的最有趣的分子，与参考竞争性和非竞争性抑制剂相比，奥司他韦 (EC

  DOI：

  10.1016/j.bioorg.2021.105139

文献信息

• [EN] THERAPEUTIC AURONES<br/>[FR] AURONES THÉRAPEUTIQUES
  申请人：MIDDLE TENNESSEE STATE UNIV

  公开号：WO2017180644A1

  公开（公告）日：2017-10-19

  Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

  发现替代的金莲素具有抗锥虫、抗真菌和免疫调节活性。该发明提供了新型金莲素化合物、药物组合物和方法，涵盖医学和兽医应用。
• Therapeutic aurones
  申请人：MIDDLE TENNESSEE STATE UNIVERSITY

  公开号：US10899727B2

  公开（公告）日：2021-01-26

  Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

  研究发现，取代的醛酮具有抗锥虫、抗真菌和免疫调节活性。本发明提供了新型醛酮化合物、药物组合物和方法，包括医疗和兽医应用。
• THERAPEUTIC AURONES
  申请人：Middle Tennessee State University

  公开号：EP3442520A1

  公开（公告）日：2019-02-20
• In quest of small-molecules as potent non-competitive inhibitors against influenza
  作者：Khushboo Malbari、Priyanka Saha、Mamta Chawla-Sarkar、Shanta Dutta、Swita Rai、Mamata Joshi、Meena Kanyalkar

  DOI：10.1016/j.bioorg.2021.105139

  日期：2021.9

  neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting

  一系列支架，即 aurones、3-indolinones、4-quinolones 和肉桂酸-哌嗪杂化物，被设计、合成并在体外针对 A/H1N1pdm09 病毒进行了研究。与分子对接研究中的唾液酸和奥司他韦不同，设计的分子采用不同的结合方式，即在神经氨酸酶的430-cavity中。所有分子都降低了病毒滴度并表现出非细胞毒性以及对 MDCK 细胞的冷冻保护特性。分子 ( Z )-2-(3'-Chloro-benzylidene)-1,2-dihydro-indol-3-one ( 2f ), ( Z )-2-(4'-Chloro-benzylidene)-1,2- dihydro-indol-3-one ( 2g ) 和 2-(2'-Methoxy-phenyl)-1H-quinolin-4-one ( 3a) 是本研究中鉴定出的最有趣的分子，与参考竞争性和非竞争性抑制剂相比，奥司他韦 (EC
• Novel Pyridazino[4,3-<i>b</i>]indoles with Dual Inhibitory Activity against <i>Mycobacterium </i><i>t</i><i>uberculosis</i> and Monoamine Oxidase
  作者：Valeriya S. Velezheva、Patrick J. Brennan、Vladimir Yu. Marshakov、Dmitrij V. Gusev、Inessa N. Lisichkina、Alexander S. Peregudov、Larisa N. Tchernousova、Tatiana G. Smirnova、Sofia N. Andreevskaya、Alexei E. Medvedev

  DOI：10.1021/jm030479g

  日期：2004.6.1

  Tuberculosis is one of the most common infectious diseases known to man. About 37% of the world's population (about 1.86 billion people) are infected with Mycobacterium tuberculosis. According to the World Health Organization, every year approximately 8 million people develop active tuberculosis and almost 2 million of those die from the disease. The incidence of multidrug-resistant tuberculosis (MDR-TB) is increasing. The present drug regimen for treating tuberculosis has been in existence for 30 years. New drugs that will shorten total treatment duration, improve the treatment of MDR-TB, and address latent tuberculosis are the most urgent need of tuberculosis control programs. A new series of synthetic 3-amino-4-arylpyridazino[4,3-b]indoles (pyridazinoindoles) were identified as inhibitors of Mycobacterium tuberculosis. The design, synthesis, and antimycobacterial activity of these compounds are described. While the most active compounds are still not comparable to the front-line drugs rifampicin and isoniazid, they do show promise. Most of the pyridazinoindoles with appreciable antituberculosis activity also inhibit monoamine oxidase, suggestive of a novel inhibitory effect on mycobacterial redox reactions.