5,6-二氢-咪唑并[2,1-b]噻唑-3-酮 | 6703-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5,6-二氢-咪唑并[2,1-b]噻唑-3-酮
• 英文名称: 5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one
• 英文别名: 2,3,5,6-Tetrahydroimidazo<2,1-b>thiazol-3-on；5,6-dihydro-imidazo[2,1-b]thiazol-3-one；5,6-Dihydro-imidazo[2,1-b]thiazol-3-on；5,6-dihydroimidazo [2,1-b]thiazole-3-(2H)-one；5,6-Dihydro-imidazo[2,1-b]thiazol-3-one；5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-one
• CAS: 6703-51-1
• 化学式: C₅H₆N₂OS
• mdl: MFCD00457420
• 分子量: 142.181
• InChiKey: RZBBCLQHSBMRHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58
• 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：

  5,6-二氢-咪唑并[2,1-b]噻唑-3-酮 在 H₂O₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 cis,mer-[Pt(NH3)2(C5H6N2OS)Cl3]Cl
  参考文献：
  名称：

  含咪唑并噻唑配体的铂三胺配合物的合成，表征和抗肿瘤活性

  摘要：

  摘要制备了一系列铂（II）和铂（IV）三胺配合物，并对其进行了表征和评价，认为它们是潜在的抗肿瘤药物。络合物为[PtA 2（N-het）Cl] +或[PtA 2（N-het）Cl 3] +形式的顺式或反式异构体，其中A是单齿胺，NH 3或A 2是二齿胺，乙二胺（en）和N-het是咪唑并噻唑或衍生物。[Pt（en）（C 5 H 6 N 2 OS）Cl] NO 3（5b）和[Pt（en）（C 5 H 6 N 2 OS）Cl 3] NO 3两种铂配合物的结构（5e）通过单晶X射线衍射测定。络合物5b的晶体在空间群Pna2 1中为正交晶体，a = 9.2451（7），b = 18.950（2），c = 7.908（2）A，Z = 4。复数5e的那些在空间群P（-1）中为三斜线，a = 8.2884（9），b = 10.853（1），c = 11.244（2）A，α= 72.50（1），β= 70

  DOI：

  10.1016/s0020-1693(96)05453-9
• 作为产物：
  描述：

  2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 5,6-二氢-咪唑并[2,1-b]噻唑-3-酮
  参考文献：
  名称：

  Reactions of Ethylenethiourea with α- and β-Halo Acids and Derivatives¹

  摘要：

  DOI：

  10.1021/jo01030a013

文献信息

• Structures of Addition Products of Acetylenedicarboxylic Acid Esters with Various Dinucleophiles. An application of C, H-spin-coupling constants
  作者：Ulrich Vögeli、Wolfgang von Philipsborn、Kuppuswamy Nagarajan、Mohan D. Nair

  DOI：10.1002/hlca.19780610207

  日期：1978.3.8

  Heterocyclic compounds obtained by addition of acetylenedicarboxylic acid esters to thioureas, cyclic amidines and o-difunctionalized aromatic systems have been studied by 13C-NMR. In particular, C, H-spin-coupling constants over two and three bonds were used to differentiate between the various constitutional isomers and to establish the configuration of trisubstituted exocyclic C, C-double bonds

  通过13 C-NMR研究了通过将乙炔二羧酸酯加到硫脲，环am和邻双官能化的芳族体系中得到的杂环化合物。特别地，在两个和三个键上的C，H-自旋偶联常数用于区分各种结构异构体并建立三取代的外环C，C-双键的构型。邻位顺式和反式C，H-spin偶联的构型意义和诊断价值在本系列中再次得到证明。
• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• 2,3,5,6-Tetrahydro- and 5,6-dihydro-imidazo[2,1-b]thiazoles from imidazoline-2-thiol derivatives and unsaturated or halogenated acids and esters
  作者：R. B. Blackshire、C. J. Sharpe

  DOI：10.1039/j39710003602

  日期：——

  imidazoline-2-thiol with maleic anhydride and with α-bromo-dicarboxylic acids and their diethyl esters. Ethyl 2-chloro- and 4-bromoacetoacetate with imidazoline-2-thiol give derivatives of 5,6-dihydroimidazo[2,1-b]thiazole with retention of the ethoxycarbonyl group. 5-Substituted 2-thiohydantoins react in a similar way.

  证据表明，咪唑啉-2-硫醇与乙炔二羧酸及其二甲基酯的反应产物是5，6-二氢咪唑并[ 2，1- b ]噻唑-3（2 H）-one的衍生物。该咪唑啉-2-硫醇与马来酸酐，α-溴-二羧酸及其二乙酯的反应可制得该环系的其他衍生物。用2-咪唑啉-2-巯基的2-氯乙酰乙酸乙酯和4-溴乙酰乙酸乙酯得到5,6-二氢咪唑并[2,1- b ]噻唑的衍生物，并保留了乙氧基羰基。5-取代的2-硫代乙内酰脲以相似的方式反应。
• Identification of (Z)-2-benzylidene-dihydroimidazothiazolone derivatives as tyrosinase inhibitors: Anti-melanogenic effects and in silico studies
  作者：Heejeong Choi、Il Young Ryu、Inkyu Choi、Sultan Ullah、Hee Jin Jung、Yujin Park、YeJi Hwang、Yeongmu Jeong、Sojeong Hong、Pusoon Chun、Hae Young Chung、Hyung Ryong Moon

  DOI：10.1016/j.csbj.2022.02.007

  日期：——

  that these two compounds bind more strongly to the active site of tyrosinase than kojic acid. Docking simulation results using a human tyrosinase homology model confirmed the abilities of 1b and 1f to strongly inhibit human tyrosinase. B16F10 murine melanoma cells were used to investigate whether these two compounds display tyrosinase inhibitory activities and anti-melanogenesis effects in cells. Both

  作为我们不断寻找新型酪氨酸酶抑制剂的一部分，我们基于 MHY773 的结构设计了 5,6-二氢咪唑并[ 2,1- b ]噻唑-3(2 H )-酮 (DHIT) 衍生物；一种有效的酪氨酸酶抑制剂，具有 2-iminothiazolidin-4-one 模板。在使用 Knoevenagel 缩合合成的 11 种 DHIT 衍生物中，三种 DHIT 衍生物1a (IC 50  = 36.14 ± 3.90 μM)、1b (IC 50  = 0.88 ± 0.91 μM) 和1f (IC 50  = 17.10 ± 1.01 μM) 抑制蘑菇酪氨酸酶超过曲酸 (IC 50  = 84.41 ± 2.87 μM)。值得注意的是，化合物1b对蘑菇酪氨酸酶的抑制作用分别比曲酸和 MHY773 强 100 倍和 3.3 倍。Lineweaver-Burk 图表明化合物1b和1f竞争性抑制蘑菇酪氨酸酶，并且
• Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype
  作者：Mariangela Urbano、Miguel Guerrero、Subash Velaparthi、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.09.049

  日期：2011.11

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.