2-methyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-one | 34998-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-methyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-one
• 英文别名: 2-Methyl-1-thioxo-1H-imidazo[1,5-a]indol-3(2H)-one；2-methyl-3-thioxo-2,3-dihydro-imidazo[1,5-a]indol-1-one；2-Methyl-3-thioxo-2,3-dihydro-imidazo[1,5-a]indol-1-on；1,2,3,4-Tetrahydro-1-oxo-2-methylimidazolo<3,4-α>indol-3-thion；2-Methyl-1-sulfanylideneimidazo[1,5-a]indol-3-one
• CAS: 34998-77-1
• 化学式: C₁₁H₈N₂OS
• 分子量: 216.263
• InChiKey: ABGBWPCFKXPBEU-UHFFFAOYSA-N

物化性质

• 熔点：
  188 °C
• 沸点：
  384.0±25.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-one 在 双氧水 作用下， 生成 2-methyl-2,3-dihydro-1H-imidazol[1,5-a]indole-1,3-dione
  参考文献：
  名称：

  Studies on the C₁₁H₈N₂OS Degradation Product of Gliotoxin¹

  摘要：

  DOI：

  10.1021/ja01153a026
• 作为产物：
  描述：

  邻溴苯甲醛 在 喹啉 、 sodium acetate 、 乙酸酐 、 溶剂黄146 、 copper(II) oxide 作用下， 生成 2-methyl-3-thioxo-2,3-dihydroimidazo[1,5-a]indol-1-one
  参考文献：
  名称：

  Gliotoxin. IX. Synthesis of the C₁₁H₈N₂OS Degradation Product¹

  摘要：

  DOI：

  10.1021/ja01152a056

文献信息

• Rigidified Compounds for Modulating Heparanase Activity
  申请人：Gelder M. Van Joel

  公开号：US20080039456A1

  公开（公告）日：2008-02-14

  Disclosed are novel rigidified compounds having a rhodanine-like residue and at least one aryl or heteroaryl residue linked to the rhodanine-like residue, whereby a core structure of these compounds, as defined in the specification, is characterized as having one or zero free-to-rotate bonds. Also disclosed are pharmaceutical compositions containing these rigidified compounds and uses thereof for modulating the activity of heparanase and hence in the treatment of heparanase-associated diseases and disorders, and uses thereof for modulating the activity of heparin-binding proteins and hence in the treatment of heparin-binding proteins-associated diseases and disorders as well as in the treatment of medical conditions that are at least partially treatable by rhodanine or a rhodanine analog.

  揭示了一种新颖的刚性化合物，其具有类似罗丹啉的残基和至少一个连接到类似罗丹啉残基的芳基或杂芳基残基，其中这些化合物的核心结构，如规范中定义的那样，其特征是具有一个或零个可自由旋转的键。还披露了含有这些刚性化合物的药物组合物以及用于调节肝素酶活性的用途，从而治疗与肝素酶相关的疾病和紊乱，并用于调节肝素结合蛋白的活性以及治疗与肝素结合蛋白相关的疾病和紊乱，以及治疗至少部分可通过罗丹啉或罗丹啉类似物治疗的医疗状况的用途。
• Novel Synthesis of Bicycles with Fused Pyrrole, Indole, Oxazole, and Imidazole Rings
  作者：Alan R. Katritzky、Sanjay K. Singh、Sergey Bobrov

  DOI：10.1021/jo0485334

  日期：2004.12.1

  Reactions of benzotriazol-1-yl(1H-pyrrol-2-yl)methanone 10 and benzotriazol-1-yl(1H-indol-2-yl)methanone 11 with diverse ketones, isocyanates, and isothiocyanates in the presence of base afforded pyrrolo[1,2-c]oxazol-1-ones 1, oxazolo[3,4-a]indol-1-ones 2, pyrrolo[1,2-c]imidazoles 3, and imidazo[1,5-a]indoles 4 by a simple one-step procedure.

  在碱存在下，苯并三唑-1-基（1 H-吡咯-2-基）甲酮10和苯并三唑-1-基（1 H-吲哚-2-基）甲酮11在碱的存在下与各种酮，异氰酸酯和异硫氰酸酯的反应得到吡咯并[1,2 - c ]恶唑-1-酮1，恶唑并[3,4- a ]吲哚-1-酮2，吡咯并[1,2- c ]咪唑3和咪唑并[1,5- a通过简单的一步操作即可吲哚4。
• A New Approach to Imidazo[1,5-a]indole Derivatives
  作者：Peter Kutschy、Mojmír Suchý、Milan Dzurilla、Mitsuo Takasugi、Vladimír Kováčik

  DOI：10.1135/cccc20001163

  日期：——

  Reaction of indole-2-carbonyl isothiocyanate (1) with sodium methanethiolate afforded 1-thioxo-1H-imidazo[1,5-a]indol-3(2H)-one (3). Its methylation with methyl iodide in the presence of lithium hydride in dimethylformamide, or potassium carbonate in acetone resulted in the formation of corresponding S- and N-methyl derivatives 4 and 5. N-(Indole-2-carbonyl)thiocarbamates and N-(indole-2-carbonyl)thioureas prepared by treatment of isothiocyanate 1 with corresponding nucleophilic reagents were S-methylated with methyl iodide in acetone in the presence of potassium carbonate. The obtained N-(indole- 2-carbonyl) substituted thiocarbonimidates 15, 16 and isothioureas 17-20 afforded by treatment with lithium hydride in dimethylformamide the derivatives of imidazo[1,5-a]- indol-3-one 23-28 in 49-87% yields. Antifungal activity of the prepared compounds has been examined, using the fungus Bipolaris leersiae. 1-Methylsulfanyl-3H-imidazo-[1,5-a]- indol-3-one (4) exhibited the highest antifungal activity.

  吲哚-2-羰基异硫氰酸酯（1）与甲硫醇钠反应生成1-硫代-1H-咪唑[1,5-a]吲哚-3(2H)-酮（3）。在二甲基甲酰胺中加入氢化锂或在丙酮中加入碳酸钾，甲基化反应使其形成相应的S-甲基和N-甲基衍生物4和5。通过用相应的亲核试剂处理异硫氰酸酯1，制备了吲哚-2-羰基硫脲酸酯和吲哚-2-羰基硫脲，用碳酸钾在丙酮中进行S-甲基化反应。用氢化锂在二甲基甲酰胺中处理得到N-(吲哚-2-羰基)取代硫氨酸酯15、16和异硫脲酸酯17-20，产率为49-87%。使用真菌Bipolaris leersiae测试了所制备化合物的抗真菌活性。1-甲基硫基-3H-咪唑[1,5-a]吲哚-3-酮（4）表现出最高的抗真菌活性。
• Elvidge; Spring, Journal of the Chemical Society, 1949, p. Spl. 135, 138
  作者：Elvidge、Spring

  DOI：——

  日期：——
• Gliotoxin. VI. The Nature of the Sulfur Linkages. Conversion to Desthiogliotoxin^1,2
  作者：James D. Dutcher、John R. Johnson、William F. Bruce

  DOI：10.1021/ja01226a037

  日期：1945.10