N-(1,3-苯并噻唑-2-基)-3-氯丙酰胺 | 2877-36-3

• 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-(1,3-苯并噻唑-2-基)-3-氯丙酰胺
• 中文别名: N-苯并噻唑-2-基-3-氯-丙酰胺
• 英文名称: β-chloropropionyl-2-aminobenzothiazole
• 英文别名: N-2-Benzothiazolyl-3-chlorpropionamid；2-<3-Chlorpropionylamino>-benzthiazol；2-(3-Chlorpropionylamino)-benzthiazol；2-(β-Chlorpropionamido)benzothiazol；N-benzothiazol-2-yl-3-chloro-propionamide；2-(β-Chlorpropionylamino)-benzthiazol；2-(β-Chlor-propionyl)-benzothiazol；N-(1,3-benzothiazol-2-yl)-3-chloropropanamide
• CAS: 2877-36-3
• 化学式: C₁₀H₉ClN₂OS
• mdl: MFCD01213665
• 分子量: 240.713
• InChiKey: BDRXIJMJSBTEBN-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C(Solv: ethanol (64-17-5); acetone (67-64-1))
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N-(1,3-苯并噻唑-2-基)-3-氯丙酰胺 生成 2-oxo-1,2,3,4-tetrahydro-benzo[4,5]thiazolo[3,2-a]pyrimidinylium; chloride
  参考文献：
  名称：

  Preparation and ring opening of 1,2,3,4-tetrahydro-2-oxopyrimido[2,1-b]benzothiazol-5-ium chloride

  摘要：

  DOI：

  10.1021/jo00829a072
• 作为产物：
  描述：

  苯胺 在 甲酸 、 溴 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(1,3-苯并噻唑-2-基)-3-氯丙酰胺
  参考文献：
  名称：

  Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

  摘要：

  Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.09.068

文献信息

• Synthesis, physicochemical characterization, cytotoxicity, antimicrobial, anti-inflammatory and psychotropic activity of new N-[1,3-(benzo)thiazol-2-yl]-ω-[3,4-dihydroisoquinolin-2(1H)-yl]alkanamides
  作者：Alla Zablotskaya、Izolda Segal、Athina Geronikaki、Tatiana Eremkina、Sergey Belyakov、Marina Petrova、Irina Shestakova、Liga Zvejniece、Vizma Nikolajeva

  DOI：10.1016/j.ejmech.2013.10.008

  日期：2013.12

  4-dihydroisoquinolin-2(1H)-yl]ethanamide is reported to determine its conformational feature. The investigated compounds were found to be active in psychotropic in vivo, anti-inflammatory in vivo and cytotoxicity in vitro screening. They possess marked sedative action, reveal high anti-inflammatory activity, have selective cytotoxic effects and NO-induction ability concerning tumour cell lines. Some of

  合成了一系列新的N -[（苯并）噻唑-2-基] -2 / 3- [3,4-二氢异喹啉-2（1 H）-基]乙烷/丙酰胺衍生物，并用1 H，13 C表征NMR和IR光谱学和质谱。据报道，N-（1,3-苯并噻唑-2-基）-2- [3,4-二氢异喹啉-2（1 H）-基]乙酰胺的单晶X射线研究确定了其构象特征。发现所研究的化合物在体内具有精神活性，在体内具有抗炎作用，并且在体外具有细胞毒性。筛选。它们具有明显的镇静作用，具有很高的抗炎活性，对肿瘤细胞系具有选择性的细胞毒作用和NO诱导能力。某些合成的化合物显示出抗菌作用。试图使生物学结果与其结构特征和理化参数相关联。已经揭示了合成化合物的活性类型的一些特定组合。
• Concise Synthesis of the Isothiourea Organocatalysts Homobenzotetramisole and Derivatives
  作者：Beatrice Ranieri、Omar Robles、Daniel Romo

  DOI：10.1021/jo400603n

  日期：2013.6.21

  A concise approach to the synthesis of homobenzotetramisole and derivatives is described. Our strategy features a one-pot acylation–cyclization of 2-aminobenzothiazole with α,β-unsaturated acid chlorides to afford annulated pyrimidones. Subsequent Grignard addition followed by acid-promoted dehydration and reduction provides good overall yields of the title compounds in three steps and in quantities

  描述了合成高苯并四咪唑及其衍生物的简明方法。我们的策略的特点是将一锅法酰化-将2-氨基苯并噻唑与α，β-不饱和酰氯进行环化反应，以提供环化的嘧啶酮。随后加入格氏试剂，然后进行酸促进的脱水和还原反应，分三步进行，以最高10 g的量提供了良好的标题化合物总收率。该合成使用低成本且容易获得的起始原料，并且在手性分离后能够接触这些越来越有用的亲核催化剂的两个光学对映体。
• Benzothiazole‐Propanamide Linker Pyrrolidine (Morpholine) as Monoamine Oxidase‐B and Butyrylcholinesterase Inhibitors
  作者：Zhi‐Wen He、B. S. Kai‐Yin Jiang、Xin‐Hao Sun、Min Tang、Ya‐Wen Liu、Li‐Ping Guan、Di Wu

  DOI：10.1002/cbdv.202301271

  日期：2023.12

  exhibited selective MAO-B inhibitory effects with inhibition rates of 60.10 % and 66.30 % at 100 μM, respectively. In contrast, all designed derivatives were poor active against AChE and MAO-A at a concentration of 100 μM. The toxicity analysis in vitro by MTT and AO/EB fluorescence staining confirmed that 2 c and 2 h were nontoxic up to 100 μM. Molecular modeling studies showed that 2 c and 2 h could

  根据融合技术创建有效的多靶点定向配体，本研究设计并合成了一系列苯并[ d ]噻唑-2-基)-3-(吡咯烷-1-基)或3-(形态- olino-1-yl)丙酰胺衍生物，并通过体外酶效应测定评估其对 MAOs、AChE、BuChE 的抑制效力。根据活性结果，我们发现衍生物N- (5-甲基苯并[ d ]噻唑-2-基)-3-(吡咯烷-1-基)丙酰胺( 2c )和N- (6-溴苯并[ d ]噻唑) -2-yl)-3-(吡咯烷-1-基)丙酰胺 ( 2 h ) 对 BuChE 显示出良好的抑制效力，IC 50值分别为 15.12 μM 和 12.33 μM。此外， 2 c和2 h还表现出选择性 MAO-B 抑制作用，在 100 μM 时抑制率分别为 60.10 % 和 66.30 %。相比之下，所有设计的衍生物在浓度为 100 μM 时对 AChE 和 MAO-A 的活性都很差。通过MTT和AO/EB荧光染色进行的体外毒性分析证实，在100
• Novel schistosomicides. S-2-{[2-(2-Thiazolylcarbamoyl)ethyl]amino}ethyl hydrogen thiosulfate and related compounds
  作者：Roger D. Westland、Leslie M. Werbel、John R. Dice、Joyce L. Holmes、Barbara G. Zahm

  DOI：10.1021/jm00292a006

  日期：1971.10
• Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine
  作者：Christina Papadopoulou、Athina Geronikaki、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.farmac.2005.06.014

  日期：2005.11

  A series of thiazolyl-N-phenyl piperazines has been synthesised and tested for anti-inflammatory activity. Their R(M) values were determined as an expression of their lipophilicity. Theoretical calculation of their lipophilicity, as clog P and logPsk also performed. The effect of the synthesised compounds on inflammation, using the carrageenin induced mouse paw oedema model was studied. In general, the studied compounds were found to be potent anti-inflammatory agents (44-74.1%). Anti-inflammatory activity was influenced by some structural characteristics of the synthesised compounds. An attempt was made to correlate their biological activity with some physicochemical parameters using a quantitative structure-activity relationship approach (QSAR).