2,6-二甲基咪唑并[2,1-b][1,3]噻唑-5-甲醛 | 102410-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 中文名称: 2,6-二甲基咪唑并[2,1-b][1,3]噻唑-5-甲醛
• 英文名称: 2,6-dimethyl-5-formylimidazo<2,1-b>thiazole
• 英文别名: 2,6-Dimethylimidazo<2,1-b>thiazole-5-carboxaldehyde；2,6-dimethylimidazo[2,1-b]thiazole-5-carboxaldehyde；2,6-Dimethylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 102410-25-3
• 化学式: C₈H₈N₂OS
• mdl: MFCD07850250
• 分子量: 180.23
• InChiKey: QYPQGPDZMPQWMT-UHFFFAOYSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 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：

  2,6-二甲基咪唑并[2,1-b][1,3]噻唑-5-甲醛 在 sodium tetrahydroborate 作用下， 以55%的产率得到(2,6-二甲基咪唑并[2,1-b][1,3]噻唑-5-基)甲醇
  参考文献：
  名称：

  Andreani, Aldo; Rambaldi, Mirella; Carloni, Patricia, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 525 - 529

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-dimethylimidazolo<2,1-b>thiazole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 以65%的产率得到2,6-二甲基咪唑并[2,1-b][1,3]噻唑-5-甲醛
  参考文献：
  名称：

  Synthesis and diuretic activity of imidazo[2,1-b]thiazole acetohydrazones

  摘要：

  DOI：

  10.1016/0223-5234(87)90169-3

文献信息

• Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and Study of Their Effect on the Cell Cycle
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Vida Garaliene、William Welsh、Sonia Arora、Giovanna Farruggia、Lanfranco Masotti

  DOI：10.1021/jm050353e

  日期：2005.8.1

  This paper reports the synthesis of a new series of 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones which were tested as potential antitumor agents at the National Cancer Institute. Two derivatives are now under review by BEC (Biological Evaluation Committee of NCI). To investigate the mechanism of action, the effect on cell cycle progression was studied by monitoring them in colon adenocarcinoma

  本文报道了一系列新的3-（5-咪唑并[2,1-b]噻唑基亚甲基）-2-吲哚满酮的合成方法，这些化合物已在美国国家癌症研究所测试为潜在的抗肿瘤药物。BEC（NCI生物评估委员会）目前正在审查两种衍生物。为了研究其作用机理，通过在结肠腺癌HT-29中监测它们来研究其对细胞周期进程的影响：两者均能够阻断有丝分裂中的HT-29。3-[（2,6-二甲基咪唑并[2,1-b]噻唑-5-基）亚甲基] -5-氯-2-吲哚满酮是活性最高的化合物。
• 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。
• Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action
  作者：Aldo Andreani、Massimiliano Granaiola、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Giovanna Farruggia、Claudio Stefanelli、Lanfranco Masotti、Tam L. Nguyen、Ernest Hamel、Robert H. Shoemaker

  DOI：10.1021/jm2012694

  日期：2012.3.8

  The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.
• Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and 3-(5-Imidazo[2,1-<i>b</i>]thiadiazolylmethylene)-2-indolinones: Selectivity against Colon Tumor Cells and Effect on Cell Cycle-Related Events
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Manuela Voltattorni、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Robert H. Shoemaker

  DOI：10.1021/jm800827q

  日期：2008.12.11

  The synthesis of new 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones is reported. The antitumor activity was evaluated according to the protocols available at the National Cancer Institute (NCI), Bethesda, MD. To investigate the mechanism of action of the most potent antitumor agent of this series, its effect on growth of HT-29 colon carcinoma cells was studied. Its ability to inhibit cellular proliferation was mediated by cell cycle arrest at the G2/M phase, accompanied by inhibition of ornithine decarboxylase (ODC), the limiting enzyme of polyamine synthesis, and followed by induction of apoptosis.
• 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.