2-氯-N-(4-苯基-噻唑-2-基)-乙酰胺 | 5039-16-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氯-N-(4-苯基-噻唑-2-基)-乙酰胺
• 英文名称: 2-chloro-N-(phenylthiazol-2-yl)acetamide
• 英文别名: 2-chloro-N-(4-phenylthiazol-2-yl)acetamide；2-Chloracetylamino-4-phenyl-thiazol；2-chloroacetamido-4-phenylthiazole；2-chloro-N-(4-phenyl-1, 3-thiazol-2-yl)acetamide；4-Phenyl-2-chloracetylamino-thiazol；2-chloro-N-(4-phenyl-1,3-thiazol-2-yl)acetamide
• CAS: 5039-16-7
• 化学式: C₁₁H₉ClN₂OS
• mdl: MFCD00124517
• 分子量: 252.724
• InChiKey: FFAWPJLADWBKCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-氯-N-(4-苯基-噻唑-2-基)-乙酰胺 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.25h， 生成 (5Z)-5-(2-oxoindolin-3-ylidene)-2-(4-phenylthiazol-2-ylimino)thiazolidin-4-one
  参考文献：
  名称：

  5-Nitro-heteroarylidene analogs of 2-thiazolylimino-4-thiazolidinones as a novel series of antibacterial agents

  摘要：

  In the pursuit of novel antibacterial agents with the 2-thiazolylimino-4-thiazolidinone as a core structure, a series of 5-nitro-heteroarylidene and 5-(2-oxoindolin-3-ylidene) analogs of 2-thiazolylimino-5-arylidene-4-thiazolidinone were synthesized and their antibacterial activities were evaluated against some strains of Gram-positive and Gram-negative bacteria, as well as Helicobacter pylori strains. Biological data indicated that 5-nitrofuran analog 5a and 5-nitroimidazole analog 7a containing no substitutions on the thiazole ring were the most potent compounds.

  DOI：

  10.1007/s00044-012-0224-6
• 作为产物：
  描述：

  2-溴苯乙酮 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-氯-N-(4-苯基-噻唑-2-基)-乙酰胺
  参考文献：
  名称：

  [N-(噻唑-2-基)氨基甲酰基]甲基膦酸二乙酯的合成与生物筛选

  摘要：

  罗兹大学的财政支持和助学金 (EOO) 和南非医学研究委员会 (SAMRC)，根据其经济竞争力和支持计划，获得国家财政部资金的支持。

  DOI：

  10.24820/ark.5550190.p010.534

文献信息

• Utilization of α-halocarbonyl compounds in the synthesis of thiazole, thiadiazole, and thiophene derivatives
  作者：Ehab Abdel-latif、Samir Bondock

  DOI：10.1002/hc.20206

  日期：2006.4

  toward a variety of several α-halo- carbonyl compounds was investigated. Thus, reaction of 1 with α-bromoketones, hydrazonoyl bromides, and 2-chloro-N-arylacetamides afforded the corresponding dihydrothiazole, 1,3,4-thiadiazole, and thiophene derivatives, respectively. The synthesis of thiazolidin-4-one 11, thiazolidin-5-one 12, and some azo derivatives of thiazolidin-5-one were described. 5-Arylazothiazoles

  研究了 2-苯基硫代氨基甲酰乙酸乙酯 1 对多种 α-卤代羰基化合物的行为。因此，1 与 α-溴酮、腙酰溴和 2-氯-N-芳基乙酰胺反应分别得到相应的二氢噻唑、1,3,4-噻二唑和噻吩衍生物。描述了 thiazolidin-4-one 11、thiazolidin-5-one 12 和 thiazolidin-5-one 的一些偶氮衍生物的合成。5-芳基偶氮噻唑 17 和 19 是通过腙酰溴 3 与不同硫脲衍生物的缩合反应合成的。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:299–305, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20206
• Synthesis, biological evaluation, and docking studies of novel 5,6-diaryl-1,2,4-triazine thiazole derivatives as a new class of α-glucosidase inhibitors
  作者：Guangcheng Wang、Zhiyun Peng、Zipeng Gong、Yongjun Li

  DOI：10.1016/j.bioorg.2018.03.015

  日期：2018.8

  A novel 5,6-diaryl-1,2,4-triazine thiazole derivatives (7a-7q) were synthesized and characterized by 1H NMR and 13C NMR and evaluated for their α-glucosidase inhibitory activity. All tested compounds displayed good α-glucosidase inhibitory activity with IC50 values ranging between 2.85 ± 0.13 and 14.19 ± 0.23 μM when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 7i (IC50 = 2

  合成了新颖的5,6-二芳基-1,2,4-三嗪噻唑衍生物（7a - 7q），并通过1 H NMR和13 C NMR对其进行了表征，并评估了其对α-葡萄糖苷酶的抑制活性。与标准阿卡波糖（IC 50  = 817.38±6.27μM）相比，所有测试化合物均显示出良好的α-葡萄糖苷酶抑制活性，IC 50值在2.85±0.13和14.19± 0.23μM之间。化合物7i（IC 50 = 2.85±0.13μM）在这一系列化合物中表现出最高的活性。为了研究这类化合物与α-葡萄糖苷酶的结合方式，进行了分子对接研究。该研究表明，这些5,6-二芳基-1,2,4-三嗪噻唑衍生物是一类新的α-葡萄糖苷酶抑制剂。
• Synthesis and free radical scavenging activity of 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamide compounds
  作者：Lucas Wolf、Natália Quoos、João C.P. Mayer、Diego de Souza、André C. Sauer、Luana Meichtry、Vandreza Bortolotto、Marina Prigol、Oscar E.D. Rodrigues、Luciano Dornelles

  DOI：10.1016/j.tetlet.2016.01.079

  日期：2016.3

  The synthesis of a new series of organochalcogen-derivatives, 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamides 5a–r, provided products in satisfactory yields, which varied from 42% to 95%. All these novel compounds were screened for their in vitro free radical scavenging activity against 2,2-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)

  合成了一系列新的有机硫属元素衍生物2-烷基/芳族硫属酰基-N-（4-芳基-1,3-噻唑-2-基）乙酰胺5a – r，所提供的产品收率令人满意，从42％达到95％。筛选了所有这些新型化合物的体外对2,2-二苯基-2-吡啶并肼基（DPPH）和2,2'-叠氮基-双-（3-乙基苯并噻唑啉-6-磺酸）（ABTS）的自由基清除活性部首。化合物5（m，h，i，f，q，g，l，c，n）是对ABTS自由基物种的有效清除剂，但对DPPH自由基的清除效果较差，表明这些化合物的抗氧化作用与质子化自由基清除剂活性有关。
• 2-AMINOTHIAZOLE DERIVATIVE, PREPARATION METHOD, AND USE
  申请人：Huazhong University of Science and Technology

  公开号：EP2682390A1

  公开（公告）日：2014-01-08

  The present invention relates to the preparation of a 2-aminothiazole derivative having a structure as formula (I) and a therapeutic effect thereof for Alzheimer's disease (AD), and a therapeutic effect thereof against transplant rejection, autoimmune diseases, ischemia-reperfusion injury, chronic inflammation response, endotoxemia, and other diseases.

  本发明涉及制备具有如下式（I）结构的2-氨基噻唑衍生物及其对阿尔茨海默病（AD）的治疗效果，以及其对移植排斥、自身免疫疾病、缺血再灌注损伤、慢性炎症反应、内毒素血症和其他疾病的治疗效果。
• Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors
  作者：Anita Nasli Esfahani、Aida Iraji、Amir Alamir、Shahram Moradi、Mohammad Sadegh Asgari、Samanesadat Hosseini、Somayeh Mojtabavi、Ensieh Nasli-Esfahani、Mohammad Ali Faramarzi、Fatemeh Bandarian、Bagher Larijani、Haleh Hamedifar、Mir Hamed Hajimiri、Mohammad Mahdavi

  DOI：10.1007/s11030-021-10310-7

  日期：2022.8

  A novel series of phenoxymethybenzoimidazole derivatives (9a-n) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC50 values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC50 = 750.0 ± 10.0 μM). Enzyme kinetic studies on 9c, 9g, and 9m as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.

  一系列新型苯氧甲基苯并咪唑衍生物（9a-n）被合理设计、合成并评估了其α-葡萄糖苷酶抑制活性。所有测试化合物都表现出良好的α-葡萄糖苷酶抑制潜力，其IC50值在6.31至49.89 μM范围内，相比之下标准药物阿卡波糖的IC50值为750.0 ± 10.0 μM。对最具效力的化合物9c、9g和9m进行的酶动力学研究表明，这些化合物是不竞争性抑制剂，能够进入α-葡萄糖苷酶。分子对接研究证实，合成的化合物中的苯并咪唑和三唑环对于恰当地适应α-葡萄糖苷酶的活性位点起着重要作用。本研究表明，这一骨架可被视为高效的α-葡萄糖苷酶抑制剂。