N-1,2-苯并异噻唑-3-基-2-氯乙酰胺 | 69504-29-6

• 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: N-1,2-苯并异噻唑-3-基-2-氯乙酰胺
• 英文名称: 3-(chloroacetyl)amino-1,2-benzisothiazole
• 英文别名: 2-chloro-N-benzo[d]isothiazol-3-yl acetamide；N-1,2-Benzisothiazol-3-yl-2-chloroacetamide；N-(1,2-benzothiazol-3-yl)-2-chloroacetamide
• CAS: 69504-29-6
• 化学式: C₉H₇ClN₂OS
• 分子量: 226.686
• InChiKey: RBVVQDIPVOTOHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  N-1,2-苯并异噻唑-3-基-2-氯乙酰胺 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-(1,2-benzothiazol-3-ylamino)-5-benzylidene-1,3-thiazol-4-one
  参考文献：
  名称：

  Heteroarylimino-4-thiazolidinones as inhibitors of cartilage degradation

  摘要：

  2-Benzo[d]thiazolyl- and 2-benzo[d]isothiazolyl-imino-5-benzylidene-4-thiazolidinone derivatives were investigated as potential metalloproteinases (MMPs) inhibitors and evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1 beta, using an experimental model that reproduces the mechanisms involved in osteoarthritic (OA) diseases. Cell viability, the amount of glycosaminoglycans (GAGs) and the production of nitric oxide (NO) were measured. The most potent compound, 5-(4-methoxy-benzylidene)-2-(benzo[d]isothiazol-3-ylimino)-thiazolidin-4-one (4b), a MMP-13 inhibitor at nanomolar concentration (IC50 = 0.036 mu M), could be considered as a lead compound for the development of novel clinical agents, inhibitors of cartilage degradation, for the treatment of OA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.11.002
• 作为产物：
  描述：

  3-氨基-1,2-苯并异噻唑 、 氯乙酰氯 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-1,2-苯并异噻唑-3-基-2-氯乙酰胺
  参考文献：
  名称：

  Heteroarylimino-4-thiazolidinones as inhibitors of cartilage degradation

  摘要：

  2-Benzo[d]thiazolyl- and 2-benzo[d]isothiazolyl-imino-5-benzylidene-4-thiazolidinone derivatives were investigated as potential metalloproteinases (MMPs) inhibitors and evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1 beta, using an experimental model that reproduces the mechanisms involved in osteoarthritic (OA) diseases. Cell viability, the amount of glycosaminoglycans (GAGs) and the production of nitric oxide (NO) were measured. The most potent compound, 5-(4-methoxy-benzylidene)-2-(benzo[d]isothiazol-3-ylimino)-thiazolidin-4-one (4b), a MMP-13 inhibitor at nanomolar concentration (IC50 = 0.036 mu M), could be considered as a lead compound for the development of novel clinical agents, inhibitors of cartilage degradation, for the treatment of OA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.11.002

文献信息

• Vicini; Amoretti; Chiavarini, Il Farmaco, 1990, vol. 45, # 9, p. 933 - 943
  作者：Vicini、Amoretti、Chiavarini、Impicciatore

  DOI：——

  日期：——
• 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: Synthesis and structure–activity relationship
  作者：Paola Vicini、Athina Geronikaki、Matteo Incerti、Franca Zani、John Dearden、Mark Hewitt

  DOI：10.1016/j.bmc.2008.02.001

  日期：2008.4.1

  2-Heteroarylimino-5-benzylidene-4-thiazolidinones, unsubstituted or carrying hydroxy, methoxy, nitro and chloro groups on the benzene ring, were synthesised and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria, yeasts and mould. The antimicrobial activity of the 2-benzo[d] thiazolyl-and of the 2-benzo[d] isothiazolyl-imino-5-benzylidene- 4-thiazolidinones is, on the whole, lower in comparison with the high activity detected for the derivatives of the 2-thiazolylimino5- benzylidene-4-thiazolidinone class. Nevertheless most of the benzo[d] thiazole analogues display good inhibition of the growth of Gram positive bacilli and staphylococci, including methicillin-resistant Staphylococcus strains. Among the 2-benzo[d] isothiazole analogues a few derivatives show a strong and selective activity against bacilli. Moreover, it is worth noting that the replacement of the thiazole nucleus for the benzo[d] thiazole bicyclic system in the parent 2-(benzo[d] thiazol-2-ylimino) thiazolidin-4-one leads to significant antifungal properties against both yeasts and moulds, properties not shown by the analogous 2-thiazolyl-and 2-benzo[d] isothiazolyl-imino) thiazolidin-4-ones. The structure-activity relationship of 33 analogues possessing the 2-heteroarylimino-4- thiazolidinone structure is analysed through QSAR models. (C) 2008 Elsevier Ltd. All rights reserved.
• 2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action
  作者：A. Geronikaki、P. Eleftheriou、P. Vicini、I. Alam、A. Dixit、A. K. Saxena

  DOI：10.1021/jm8004306

  日期：2008.9.11

  SHP-2, a nonreceptor protein tyrosine phosphatase encoded by the PTPN11 gene, mediates cell signaling by growth factors and cytokines via the RAS/MAP kinase pathway. Somatic mutations in PTPN11 gene account for approximately 18% of juvenile myelomonocytic leukemia (JMML) patients. Moreover, SHP-2 mutations leading to continuously active enzyme were found in more than 50% of Noonan syndrome patients and are considered to be responsible for the high tendency of these patients to juvenile leukemias and other cancer types. Recently SHP-2 became a new drug target, but till flow little has been done in this field. In the present study, 172-thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones divided into three series of derivatives bearing thiazole-, benzo[d]thiazole-, and benzo[d]isothizole rings were tested for SHP-2 inhibitory activity. Most of the compounds were good SHP-2 inhibitors. Benzo[d]thiazole derivatives exhibited the best inhibitory action. Docking studies revealed that hydrophobic interactions and hydrogen bond formation stabilize enzyme-inhibitor complex.
• Fragment-based design, docking, synthesis, biological evaluation and structure–activity relationships of 2-benzo/benzisothiazolimino-5-aryliden-4-thiazolidinones as cycloxygenase/lipoxygenase inhibitors
  作者：Phaedra Eleftheriou、Athina Geronikaki、Dimitra Hadjipavlou-Litina、Paola Vicini、Olga Filz、Dmitry Filimonov、Vladimir Poroikov、Shailendra S. Chaudhaery、Kuldeep K. Roy、Anil K. Saxena

  DOI：10.1016/j.ejmech.2011.10.029

  日期：2012.1

  Balanced modulation of several targets is one of the current strategies for the treatment of multi-factorial diseases. Based on the knowledge of inflammation mechanisms, it was inferred that the balanced inhibition of cyclooxygenase-1/cyclooxygenase-2/lipoxygenase might be a promising approach for treatment of such a multifactorial disease state as inflammation. Detection of fragments responsible for interaction with enzyme's binding site provides the basis for designing new molecules with increased affinity and selectivity. A new chemoinformatics approach was proposed and applied to create a fragment library that was used to design novel inhibitors of cycloxygenase-1/cycloxygenase-2/lipoxygenase enzymes. Potential binding sites were elucidated by docking. Synthesis of novel compounds, and the in vitro/in vivo biological testing confirmed the results of computational studies. The benzothiazolyl moiety was proved to be of great significance for developing more potent inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.
• VICINI, P.;AMORETTI, L.;CHIAVARINI, M.;IMPICCIATORE, M., FARMACO, 45,(1990) N, C. 933-944
  作者：VICINI, P.、AMORETTI, L.、CHIAVARINI, M.、IMPICCIATORE, M.

  DOI：——

  日期：——