4-methyl-2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile | 852399-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-methyl-2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile
• 英文别名: 4-methyl-2-sulfanylidene-1,5,6,7-tetrahydrocyclopenta[b]pyridine-3-carbonitrile
• CAS: 852399-78-1
• 化学式: C₁₀H₁₀N₂S
• mdl: MFCD06655519
• 分子量: 190.269
• InChiKey: VQJXGYMFSRCMKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯乙酰胺 、 4-methyl-2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 3-amino-4-methyl-6,7-dihydro-5H-cyclopenta[b]thieno[3,2-e]pyridine-2-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors

  摘要：

  Cdc7 kinase plays a critical role in the regulation of DNA replication in eukaryotic cells and has been proposed as a target for cancer therapy. We have identified a class of Cdc7/Dbf4 inhibitors with a pyrido-thieno-pyrimidine core structure. Synthesis of a focused pyrido-thieno-pyrimidine library yielded potent and selective Cdc7 inhibitors with antiproliferative activity against cancer cells in vitro. Their synthesis and SAR data are presented herein. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.093
• 作为产物：
  描述：

  2-chloro-4-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile 在 sodium sulfide 作用下， 以 叔丁醇 为溶剂， 反应 0.33h， 生成 4-methyl-2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors

  摘要：

  Cdc7 kinase plays a critical role in the regulation of DNA replication in eukaryotic cells and has been proposed as a target for cancer therapy. We have identified a class of Cdc7/Dbf4 inhibitors with a pyrido-thieno-pyrimidine core structure. Synthesis of a focused pyrido-thieno-pyrimidine library yielded potent and selective Cdc7 inhibitors with antiproliferative activity against cancer cells in vitro. Their synthesis and SAR data are presented herein. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.093

文献信息

• [EN] ACETAMIDO-AMINO AND ACETAMIDO-SULFUR DERIVATIVES AS DNA POLYMERASE THETA INHIBITORS<br/>[FR] DÉRIVÉS ACÉTAMIDO-AMINO ET ACÉTAMIDO-SOUFRE UTILISÉS EN TANT QU'INHIBITEURS DE L'ADN POLYMÉRASE THÊTA
  申请人：IDEAYA BIOSCIENCES INC

  公开号：WO2022026548A1

  公开（公告）日：2022-02-03

  Disclosed herein are certain acetamido derivatives that are DNA Polymerase Theta (Ροlθ) inhibitors of Formula (I). Also, disclosed are pharmaceutical compositions comprising such compounds and methods of treating diseases treatable by inhibition of Ροlθ such as cancer, including homologous recombination (HR) deficient cancers.

  本文披露了某些醋酰胺衍生物，其为式(I)的DNA聚合酶Theta (Ροlθ)抑制剂。同时，还披露了包括这些化合物的制药组合物和治疗可通过抑制Ροlθ治疗的疾病的方法，例如癌症，包括同源重组(HR)缺陷癌症。
• On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes
  作者：V. V. Dotsenko、S. G. Krivokolysko、V. V. Polovinko、V. P. Litvinov

  DOI：10.1007/s10593-012-0991-5

  日期：2012.5

  It has been established that the interaction of cyanothioacetamide with 2-acetylcyclohexanone, 2-acetylcyclopentanone, or their enamines (2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes) contrary to the literature data have a non-regiospecific character and leads to the formation of mixtures of 3-cyano-4-methyl-5,6-tri(tetra)methylenepyridine-2(1 H)-thiones and 3-cyano-6-methyl-4,5-tri(tetra)methylene-pyridine-2(1 H)-thiones with a predominance of the latter.
• Condensed sulfur-containing pyridine systems 3.* Construction of penta- and hexacyclic heterocyclic systems by the cascade reaction of 3-cyanopyridine-2(1H)-thiones and 3-cyano-pyridine-2(1H)-thiolates with 8-chloromethyl-3-methyl-7-(2-oxo-2-phenylethyl)xanthene
  作者：V. V. Dotsenko、D. V. Sventukh、S. G. Krivokolysko

  DOI：10.1007/s10593-012-1149-1

  日期：2012.12

  The alkylation of 3-cyanopyridine-2(1H)-thiones with 8-chloromethyl-3-methyl-7-(2-oxo-2-phenylethyl)- xanthene in a KOH-H2O-DMF system upon heating leads to the formation of pyrido-[3",2":4',5']thieno[3',2':5,6][1,4]diazepino[7,1-f]purine-2,4(3H,6H)-dione derivatives in good yields. Under milder conditions, the intermediates of the cascade reactions, namely, 2-([3-methyl-2,6-dioxo-7-(2-oxo-2-phenylethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]methyl}thio)pyridine-3-carbonitriles, can be isolated and characterized.
• Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors
  作者：Chunlin Zhao、Christian Tovar、Xuefeng Yin、Qui Xu、Ivan T. Todorov、Lyubomir T. Vassilev、Li Chen

  DOI：10.1016/j.bmcl.2008.11.093

  日期：2009.1

  Cdc7 kinase plays a critical role in the regulation of DNA replication in eukaryotic cells and has been proposed as a target for cancer therapy. We have identified a class of Cdc7/Dbf4 inhibitors with a pyrido-thieno-pyrimidine core structure. Synthesis of a focused pyrido-thieno-pyrimidine library yielded potent and selective Cdc7 inhibitors with antiproliferative activity against cancer cells in vitro. Their synthesis and SAR data are presented herein. (C) 2008 Elsevier Ltd. All rights reserved.