3-methyl-1-phenyl-1H-spiro[benzo[4,5]thiazolo[3,2-a]pyrazolo[3,4-d]pyrimidine-4,3'-indolin]-2'-one | 745797-98-2

• 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-1-phenyl-1H-spiro[benzo[4,5]thiazolo[3,2-a]pyrazolo[3,4-d]pyrimidine-4,3'-indolin]-2'-one
• 英文别名: 3a(2)-Methyl-1a(2)-phenylspiro[3H-indole-3,4a(2)(1a(2)H)-pyrazolo[3a(2),4a(2):4,5]pyrimido[2,1-b]benzothiazol]-2(1H)-one；14'-methyl-12'-phenylspiro[1H-indole-3,16'-8-thia-1,10,12,13-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-2,4,6,9,11(15),13-hexaene]-2-one
• CAS: 745797-98-2
• 化学式: C₂₅H₁₇N₅OS
• 分子量: 435.509
• InChiKey: UYESYBCZQZJRPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯苯并噻唑 在 三甲基氯硅烷 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 28.67h， 生成 3-methyl-1-phenyl-1H-spiro[benzo[4,5]thiazolo[3,2-a]pyrazolo[3,4-d]pyrimidine-4,3'-indolin]-2'-one
  参考文献：
  名称：

  High Throughput Synthesis of Extended Pyrazolo[3,4-d]dihydropyrimidines

  摘要：

  Thirteen 5-hetarylaminopyrazoles were synthesized in 62-93% yield through the arylation of 1-isopropyl- and 1-phenyl-5-aminopyrazoles with electrophilic hetarylhalides under optimized conditions. Condensation of 5-hetarylaminopyrazoles with carbonyl compounds facilitated by AcOH or Me3SiCl furnished 23 pyrazolo[3,4-d]dihydropyrimidines in 69-86% yield. The target compounds were isolated through simple crystallization. The scope and limitation of the method are discussed.

  DOI：

  10.1021/co300063x

文献信息

• Identification and validation of selective deubiquitinase inhibitors
  作者：Anthony C. Varca、Dominick Casalena、Wai Cheung Chan、Bin Hu、Robert S. Magin、Rebekka M. Roberts、Xiaoxi Liu、He Zhu、Hyuk-Soo Seo、Sirano Dhe-Paganon、Jarrod A. Marto、Douglas Auld、Sara J. Buhrlage

  DOI：10.1016/j.chembiol.2021.05.012

  日期：2021.12

  ubiquitin precursors. Despite growing interest in DUB biological function and potential as therapeutic targets, few selective small-molecule inhibitors and no approved drugs currently exist. To identify chemical scaffolds targeting specific DUBs and establish a broader framework for future inhibitor development across the gene family, we performed high-throughput screening of a chemically diverse small-molecule

  去泛素化酶 (DUB) 是一类异肽酶，通过从蛋白质底物和泛素前体催化裂解泛素来调节泛素动力学。尽管人们对 DUB 的生物学功能和作为治疗靶点的潜力越来越感兴趣，但目前几乎没有选择性小分子抑制剂，也没有批准的药物。为了识别针对特定 DUB 的化学支架并为未来跨基因家族的抑制剂开发建立更广泛的框架，我们针对八种不同的 DUB 对化学多样化的小分子文库进行了高通量筛选，跨越三个充分表征的 DUB 家族。有希望的命中化合物在一系列反筛选和正交试验中得到验证，并进一步评估了扩展 DUB 面板的选择性。通过这些努力，
• High Throughput Synthesis of Extended Pyrazolo[3,4-<i>d</i>]dihydropyrimidines
  作者：Sergey V. Ryabukhin、Dmitry S. Granat、Andrey S. Plaskon、Alexander N. Shivanyuk、Andrey A. Tolmachev、Yulian M. Volovenko

  DOI：10.1021/co300063x

  日期：2012.8.13

  Thirteen 5-hetarylaminopyrazoles were synthesized in 62-93% yield through the arylation of 1-isopropyl- and 1-phenyl-5-aminopyrazoles with electrophilic hetarylhalides under optimized conditions. Condensation of 5-hetarylaminopyrazoles with carbonyl compounds facilitated by AcOH or Me3SiCl furnished 23 pyrazolo[3,4-d]dihydropyrimidines in 69-86% yield. The target compounds were isolated through simple crystallization. The scope and limitation of the method are discussed.