5-oxo-7-[4-(propan-2-yI)phenyI]-2H,3H,5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonitrile | 136498-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-oxo-7-[4-(propan-2-yI)phenyI]-2H,3H,5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonitrile
• 英文别名: 5-oxo-7-[4-(propan-2-yl)phenyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonitrile；5-oxo-7-(4-propan-2-ylphenyl)-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonitrile
• CAS: 136498-12-9
• 化学式: C₁₆H₁₅N₃OS
• 分子量: 297.381
• InChiKey: XYWNGJVYKXCUDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-2-噻唑啉 、 氰乙酸乙酯 、 4-异丙基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以24%的产率得到5-oxo-7-[4-(propan-2-yI)phenyI]-2H,3H,5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  噻唑烷并 [3,2-a] 嘧啶衍生物的一锅法合成

  摘要：

  摘要 2-氨基噻唑啉与芳香醛和活化的亚甲基（丙二腈、丙二酸二乙酯或氰基乙酸乙酯）反应得到标题化合物。使用光谱数据和化学证明明确分配了这些结构。

  DOI：

  10.1080/00397919108016417

文献信息

• [EN] NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS NMDA ET UTILISATIONS DE CEUX-CI
  申请人：CADENT THERAPEUTICS

  公开号：WO2018119374A1

  公开（公告）日：2018-06-28

  Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.

  本文披露了部分杂芳化合物及其在治疗神经精神障碍，例如精神分裂症和重度抑郁症中的用途方法。提供了药物组合物和制备杂芳化合物的方法。这些化合物被认为可以调节NMDA受体。
• One-Pot Synthesis of Thiazolidino [3,2-a] Pyrimidine Derivatives
  作者：Edwige Jeanneau-Nicolle、Martine Benoit-Guyod、Gérard Leclerc

  DOI：10.1080/00397919108016417

  日期：1991.7

  Abstract Reaction of 2-aminothiazoline with an aromatic aldehyde and an activated methylene group (malonitrile, diethylmalonate or ethylcyanoacetate) gave the title compounds. The structures are unambiguously assigned using spectroscopic data and chemical proofs.

  摘要 2-氨基噻唑啉与芳香醛和活化的亚甲基（丙二腈、丙二酸二乙酯或氰基乙酸乙酯）反应得到标题化合物。使用光谱数据和化学证明明确分配了这些结构。
• NMDA receptor modulators and uses thereof
  申请人：Cadent Therapeutics, Inc.

  公开号：US11274107B2

  公开（公告）日：2022-03-15

  Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.

  本文部分公开了杂芳香族化合物和用于治疗神经精神疾病（如精神分裂症和重度抑郁症）的方法。提供了药物组合物和制造杂芳香族化合物的方法。这些化合物可用于调节 NMDA 受体。
• NMDA RECEPTOR MODULATORS AND USES THEREOF
  申请人：Cadent Therapeutics, Inc.

  公开号：US20200087323A1

  公开（公告）日：2020-03-19

  Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.
• New thiazolo[3,2-a]pyrimidine derivatives, synthesis and structure-activity relationships
  作者：E Jeanneau-Nicolle、M Benoit-Guyod、A Namil、G Leclerc

  DOI：10.1016/0223-5234(92)90099-m

  日期：1992.3

  Twenty-six derivatives of 5- and 7-oxo or 5- and 7-aminothiazolo[3,2-a]pyrimidines were prepared and evaluated as positive inotropic, anti-inflammatory and antihypertensive agents both in vitro and in vivo. The structures of the 5- and 7-isomers have been confirmed unambiguously by IR, UV, H-1 and C-13 NMR and MS. The structure of 1a was confirmed by the synthesis of compound 1 whose structure had been previously established by X-ray analysis. The 5-aminothiazolo-pyrimidine-6-carbonitrile derivatives 5a and 5e exhibited potent inotropic activities. 5e was more potent than the classical reference amrinone. Three compounds 5e, 5i and 5j displayed moderate antihypertensive activities. The 4-chlorophenyl derivative 5d exhibited an anti-inflammatory activity 2-fold that of aspirin. This study has demonstrated that thiazolo[3,2-a]pyrimidine compounds have interesting biological potentialities, particularly as inotropic agents, a field which had never been explored so far for this series.