3-methyl-5-formyl-6-phenylimidazo<2,1-b>thiazole | 102410-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-5-formyl-6-phenylimidazo<2,1-b>thiazole
• 英文别名: 3-methyl-5-formyl-6-phenyl-imidazo[2,1-b][1,3]thiazole；3-methyl-5-formyl-6-phenylimidazo[2,1-b]thiazole；3-Methyl-6-phenylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 102410-27-5
• 化学式: C₁₃H₁₀N₂OS
• 分子量: 242.301
• InChiKey: HDUSSFGLKVVWDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-5-formyl-6-phenylimidazo<2,1-b>thiazole 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-methyl-6-phenyl-imidazo[2,1-b][1,3]thiazole-5carbaldehyde-[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]hydrazone
  参考文献：
  名称：

  Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives

  摘要：

  Eighteen new hydrazino-1,3-thiazole derivatives were evaluated against 8 strains of multi-resistant Candida spp. Introduction of an indolyl moiety linked to the hydrazone function enhanced the in vitro anti-Candida activity, with an activity spectrum towards Candida albicans strains. Introduction of a (S)-2-aminoethyl chain on the thiazole nucleus largely enhanced the in vitro antifungal activity, with a selectivity oriented towards non-C. albicans species. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.039
• 作为产物：
  描述：

  3-methyl-6-phenyl-7H-imidazo<2,1-b>thiazolium bromide 在 sodium carbonate 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 4.0h， 生成 3-methyl-5-formyl-6-phenylimidazo<2,1-b>thiazole
  参考文献：
  名称：

  Khazi; Koti; Gadad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 393 - 398

  摘要：

  DOI：

文献信息

• Design, synthesis, anticancer evaluation and molecular docking studies of new imidazo [2, 1-b] thiazole -based chalcones
  作者：Said Dadou、Ahmet Altay、Mohammed Koudad、Burçin Türkmenoğlu、Esma Yeniçeri、Sema Çağlar、Mustapha Allali、Adyl Oussaid、Noureddine Benchat、Khalid Karrouchi

  DOI：10.1007/s00044-022-02916-9

  日期：2022.8

  A new series of imidazo[2, 1-b]thiazole-based chalcone derivatives were designed, synthesized, and tested for their anticancer activities. Firstly, the cytotoxic ability of the compounds was tested on three different types of cancer cells, namely colorectal adenocarcinoma (HT-29), lung carcinoma (A-549), breast adenocarcinoma (MCF-7), and mouse fibroblast cells (3T3-L1) by XTT tests. Afterwards, further

  设计、合成了一系列新的基于咪唑并[2, 1-b]噻唑的查尔酮衍生物，并测试了它们的抗癌活性。首先，在三种不同类型的癌细胞上测试了化合物的细胞毒能力，即结肠直肠癌 (HT-29)、肺癌 (A-549)、乳腺癌 (MCF-7) 和小鼠成纤维细胞 (3T3- L1) 通过 XTT 测试。之后，用具有最低IC 50和最高SI值的化合物3j对MCF-7细胞进行了进一步的抗癌活性研究。XTT 结果显示，所有测试化合物对癌细胞的细胞毒活性都比正常的 3T3-L1 细胞高得多。在这些化合物中，3j的 IC 50尤为突出MCF-7 细胞上的 (9.76 µM) 和 SI (14.99) 值。流式细胞术分析证明，3j处理的 MCF-7 细胞导致线粒体膜去极化、多半胱天冬酶活化，并最终导致细胞凋亡。此外，进行了计算机分子对接方法以确认实验观察并研究化合物3j的功效。通过分子对接研究研究了3j对 DNA 十二聚体和
• Imidazothiazolemethylene-acetohydrazide derivatives, preparation thereof and pharmaceutical composition having diuretic activity
  申请人：MEDIOLANUM FARMACEUTICI s.r.l.

  公开号：EP0164635A2

  公开（公告）日：1985-12-18

  Compounds of formula I wherein X, Y, n, R,, R2, R3 may have the following meanings, in all the possible combinations: X and Y, which may be the same or different, represent H, CH3, C1-C5 alkyl groups, optionally substituted, aryl groups; n is 0, 1, 2; R1 represents Cl, F, Br, C1-C6 alkyl groups, aryl and alkyl-aryl groups optionally substituted; R2 and R3, which may be the same or different represent H, CH3, alkyl groups, cycloalkyl groups, aryl-alkyl groups containing heteroatoms, heterocyclic groups optionally benzo- condensed; prepared from substituted amino-acetohydrazides and imi- dazo (2,1-b)-thiazole-5-carboxyaldehydes, have remarkable diuretic and antihypertensive activities.

  式 I 的化合物 式中 X、Y、n、R、R2、R3 在所有可能的组合中具有如下含义： X 和 Y 可以相同或不同，代表 H、CH3、C1-C5 烷基、任选取代的芳基； n 为 0、1、2； R1 代表 Cl、F、Br、C1-C6 烷基、芳基和任选取代的烷基芳基； R2 和 R3（可以相同或不同）代表 H、CH3、烷基、环烷基、含有杂原子的芳基-烷基、任选苯缩合的杂环基团； 由取代的氨基乙酰肼和咪唑（2,1-b）-噻唑-5-羧基醛制备而成，具有显著的利尿和降压活性。
• O'Daly, M. Anne; Hopkinson, Christopher P.; Meakins, G. Denis, Journal of the Chemical Society. Perkin transactions I, 1991, p. 855 - 860
  作者：O'Daly, M. Anne、Hopkinson, Christopher P.、Meakins, G. Denis、Raybould, Amanda J.

  DOI：——

  日期：——
• Synthesis and diuretic activity of imidazo[2,1-b]thiazole acetohydrazones
  作者：Aldo Andreani、Mirella Rambaldi、Giuseppe Mascellani、Pierluigi Rugarli

  DOI：10.1016/0223-5234(87)90169-3

  日期：1987.1
• Imidazo[2,1-<i>b</i>]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity
  作者：Roberta Budriesi、Pierfranco Ioan、Alessandra Locatelli、Sandro Cosconati、Alberto Leoni、Maria P. Ugenti、Aldo Andreani、Rosanna Di Toro、Andrea Bedini、Santi Spampinato、Luciana Marinelli、Ettore Novellino、Alberto Chiarini

  DOI：10.1021/jm070681+

  日期：2008.3.1

  The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1-b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.