4-methyl-2-p-tolyl-thiazole-5-carbaldehyde | 55327-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-2-p-tolyl-thiazole-5-carbaldehyde
• 英文别名: 5-Thiazolecarboxaldehyde, 4-methyl-2-(4-methylphenyl)-；4-methyl-2-(4-methylphenyl)-1,3-thiazole-5-carbaldehyde
• CAS: 55327-28-1
• 化学式: C₁₂H₁₁NOS
• mdl: MFCD09694103
• 分子量: 217.291
• InChiKey: IUBZRPNXHGEKJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-2-p-tolyl-thiazole-5-carbaldehyde 在 sodium 作用下， 以 乙醇 、 xylene 为溶剂， 生成 Ethyl 2-(4-methylphenyl)-[1,3]thiazolo[4,5-c]pyridine-6-carboxylate
  参考文献：
  名称：

  Shafiee, A.; Ghazar, H., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1171 - 1173

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-methyl-2-p-tolyl-thiazol-5-yl)-methanol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 4-methyl-2-p-tolyl-thiazole-5-carbaldehyde
  参考文献：
  名称：

  微波辅助无溶剂合成一些新型噻唑取代缩氨基硫脲类似物：抗菌和抗癌研究

  摘要：

  对抗生素耐药性的增加迫使研究人员设计针对多重耐药病原微生物的新型活性化合物。通过氨基硫脲与2-芳基-4-甲酰基噻唑、2-芳基-5-甲酰基-4-甲基噻唑和/或5-乙酰基-2-芳基-4-甲基噻唑化合物反应合成了一系列缩氨基硫脲衍生物。评估了这些基于缩氨基硫脲的噻唑加合物对结核病 H37Ra 和牛 BCG 分枝杆菌的抑制活性。他们针对两种癌细胞系评估了它们的细胞毒性：结肠癌（HCT-116）和宫颈癌（HeLa）。值得注意的是，即使在最高浓度下，这些缩氨基硫脲对这些细胞系也表现出最小的细胞毒性作用。此外，所制备的缩氨基硫脲衍生物对枯草芽孢杆菌和金黄色葡萄球菌（革兰氏阳性细菌病原体）以及大肠杆菌和荧光假单胞菌（革兰氏阴性细菌病原体）具有显着的抗菌功效。虽然大多数制备的缩氨基硫脲衍生物对白色念珠菌（一种真菌菌株）表现出中等活性，但其性能值得注意。缩氨基硫脲基噻唑加合物也采用无溶剂方法在微波辐射下成功合

  DOI：

  10.1002/bio.4587

文献信息

• Design, synthesis and biological evaluation of novel thiazole-derivatives as mitochondrial targeting inhibitors of cancer cells
  作者：Xin Dang、Shuwen Lei、Shuhua Luo、Yixin Hu、Juntao Wang、Dongdong Zhang、Dan Lu、Faqin Jiang、Lei Fu

  DOI：10.1016/j.bioorg.2021.105015

  日期：2021.9

  production assay to assess the selected compounds inhibitory effect on HeLa cells energy production. The results displayed the test compounds significantly restrained ATP production of cancer cells. Overall, we have designed and synthesized a series of compounds which exhibited significant cytotoxicity against cancer cells and effectively inhibited mitochondrial energy production.

  线粒体是细胞维持必要代谢活动的关键能量生产来源。针对功能失调的线粒体特征一直是线粒体相关疾病研究的热点。对癌性线粒体代谢的研究是肿瘤治疗中持续关注的问题。在此，我们基于我们早期对线粒体靶向剂的研究，着手评估新型 TPP-噻唑衍生物家族的抗癌活性。具体而言，我们设计并合成了一系列 TPP-噻唑衍生物，并通过 MTT 测定显示大多数合成的化合物有效抑制了三种癌细胞系（HeLa、PC3 和 MCF-7）。在结构修改后，我们探索了 SAR 关系并确定了最有希望的化合物R13（IC50 of 5.52 μM) 用于进一步研究。同时，我们进行了 ATP 产生测定以评估所选化合物对 HeLa 细胞能量产生的抑制作用。结果显示测试化合物显着抑制癌细胞的ATP产生。总体而言，我们设计并合成了一系列对癌细胞具有显着细胞毒性并有效抑制线粒体能量产生的化合物。
• Synthesis, antitubercular and antimicrobial potential of some new thiazole substituted thiosemicarbazide derivatives
  作者：Yogita K. Abhale、Abhijit Shinde、Keshav K. Deshmukh、Laxman Nawale、Dhiman Sarkar、Pravin C. Mhaske

  DOI：10.1007/s00044-017-1955-1

  日期：2017.10

  resistance due to multiple factors has warranted the need for search of new compounds which are active against multidrug resistant pathogens. In this context a small focused library of thiosemicarbazide derivatives of 2-arylthiazole-4-carbaldehyde, 4-methyl-2-arylthiazole-5-carbaldehyde and 1-(4-methyl-2-arylthiazol-5-yl) ethanone, (5a–l) has been synthesized. The title compounds were screened for inhibitory

  由于多种因素引起的抗生素耐药性的增加，保证了需要寻找对多药耐药病原体具有活性的新化合物。在这种情况下，一个小型的图书馆集中了2-芳基噻唑-4-甲醛，4-甲基-2-芳基噻唑-5-甲醛和1-（4-甲基-2-芳基噻唑-5-基）乙酮的硫代氨基脲衍生物（5a – l）已合成。筛选标题化合物对结核分枝杆菌H37Ra（ATCC 25177）和牛分枝杆菌Bacille Calmette Guerin菌株（ATCC 35743）的抑制活性。合成的化合物5a – l进一步测定了它们对两种人癌细胞系HeLa和人结肠癌116细胞系的细胞毒活性，并且在所评估的最大浓度下对这两种细胞系没有明显的细胞毒活性。此外，发现合成的化合物对革兰氏阴性菌，大肠杆菌，假单胞菌荧光和革兰氏阳性菌，金黄色葡萄球菌，枯草芽孢杆菌具有潜在的抗菌活性。大多数合成化合物对真菌菌株白色念珠菌具有中等活性。这项研究为我们正在进行的合理设计更有效的抗分枝杆菌药物的努力提供了宝贵的指导。
• Synthesis of thiazole linked chalcones and their pyrimidine analogues as anticancer agents
  作者：Chekrapani Kesari、Koteshwar Rao Rama、Khwajanezrabodin Sedighi、Jan Stenvang、Fredrik Björkling、Shravankumar Kankala、Niranjan Thota

  DOI：10.1080/00397911.2021.1884262

  日期：2021.5.3

  (2021). Synthesis of thiazole linked chalcones and their pyrimidine analogues as anticancer agents. Synthetic Communications: Vol. 51, No. 9, pp. 1406-1416.

  （2021年）。噻唑连接的查耳酮及其嘧啶类似物作为抗癌剂的合成。综合通信：第一卷。51，第9号，第1406-1416页。
• BIARYL AMINO ACIDS AND THEIR USE IN DNA BINDING OLIGOMERS
  申请人：Howard Philip Wilson

  公开号：US20110160192A1

  公开（公告）日：2011-06-30

  Compounds of formula (I): Z′-CO-A-B—NH-Z (I) wherein: Z is H or an amino protecting group; Z′ is OH, a protected or activated hydroxyl group or Cl; A is an optionally substituted C 5-6 arylene group; and B is an optionally substituted C 5-6 arylene group.

  化合物的化学式(I)：Z'-CO-A-B—NH-Z (I)，其中：Z为氢或氨基保护基；Z'为OH，受保护或活化的羟基或Cl；A为可选取代的C5-6芳基烃基；B为可选取代的C5-6芳基烃基。
• Synthesis, antimycobacterial screening and molecular docking studies of 4-aryl-4′-methyl-2′-aryl-2,5′-bisthiazole derivatives
  作者：Yogita K. Abhale、Abhijit D. Shinde、Keshav K. Deshmukh、Laxman Nawale、Dhiman Sarkar、Prafulla B. Choudhari、Santosh S. Kumbhar、Pravin C. Mhaske

  DOI：10.1007/s00044-017-1988-5

  日期：2017.11

  A series of 4-aryl-4'-methyl-2'-aryl-2,5'-bisthiazole derivatives (5a-o) were synthesized and screened for inhibitory activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis BCG (ATCC 35743) strains. Five lead compounds (5e, 5f, 5g, 5h, and 5o) were further confirmed from their dose dependent effect against MTB and Bovine-Calmette-Guerin. The most promising compounds 5f (MIC90: 11.32 mu g/mL), 5h (MIC90: 11.59 mu g/mL), and 5o (MIC90: 23.64 mu g/mL) showed strong antitubercular activity against dormant MTB and BCG as well as almost insignificant cytotoxicity up to 100 mu g/mL against HeLa, A549, and PANC-1 human cancer cell lines. Further, the synthesized compounds were found to have potential antibacterial activity against Gram-negative bacteria, Escherichia coli, Pseudomonas flurescence and Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis. Most of the synthesized compounds showed moderate activity against fungal strain Candida albicans. Molecular docking studies of these compounds showed significant interactions with crystal structure of the cytochrome P45014 alpha-sterol demethylase (CYP51) PDB ID: 1E9X. Hydrogen bond interactions with SER261 and VAL395 are important interactions for selective inhibition of designed inhibitors. Compounds 5f, 5h, and 5o showed significant interactions with 1E9X. All the experimental results promote us to consider this series as a starting point for the development of novel, selective and more potent antitubercular agents in the future.