6-phenylthieno<3,2-d>pyrimidine-2,4-dione | 36926-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 6-phenylthieno<3,2-d>pyrimidine-2,4-dione
• 英文别名: 6-phenylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione；6-phenyl-1H-thieno[3,2-d]pyrimidine-2,4-dione
• CAS: 36926-36-0
• 化学式: C₁₂H₈N₂O₂S
• 分子量: 244.274
• InChiKey: HMRVGTSOJXKKAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-phenylthieno<3,2-d>pyrimidine-2,4-dione 在 三氯氧磷 作用下， 反应 8.0h， 以93%的产率得到2,4-dichloro-6-phenylthieno[3,2-d]pyrimidine
  参考文献：
  名称：

  Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists

  摘要：

  Novel thienopyrimidine compounds 2 and 3 were discovered from high-throughput screening as Natriuretic Peptide Receptor A (NPR-A) agonists. Scaffold hopping of a thienopyrimidine ring to a quinazoline ring, introduction of the basic functional group and optimization of the substituent on the 6-position of the benzene ring of quinazoline led to improved agonistic activity. We discovered compound 48, which showed potent agonistic activity for NPR-A with an EC50 value of 0.073 mu M, indicating 350-fold potency compared to the hit compound 3. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.028
• 作为产物：
  描述：

  3-氨基-5-苯基噻吩-2-甲酸甲酯 在 氨 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 生成 6-phenylthieno<3,2-d>pyrimidine-2,4-dione
  参考文献：
  名称：

  Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists

  摘要：

  Novel thienopyrimidine compounds 2 and 3 were discovered from high-throughput screening as Natriuretic Peptide Receptor A (NPR-A) agonists. Scaffold hopping of a thienopyrimidine ring to a quinazoline ring, introduction of the basic functional group and optimization of the substituent on the 6-position of the benzene ring of quinazoline led to improved agonistic activity. We discovered compound 48, which showed potent agonistic activity for NPR-A with an EC50 value of 0.073 mu M, indicating 350-fold potency compared to the hit compound 3. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.028

文献信息

• Jourdan, Fabrice; Renault, Jacques; Karamat, Abdesselam, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 953 - 958
  作者：Jourdan, Fabrice、Renault, Jacques、Karamat, Abdesselam、Ladurie, Daniel、Robba, Max

  DOI：——

  日期：——
• Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists
  作者：Takehiko Iwaki、Yuji Nakamura、Taisaku Tanaka、Yasuyuki Ogawa、Osamu Iwamoto、Yoshihiko Okamura、Yumi Kawase、Mayumi Furuya、Yoshiaki Oyama、Takahiro Nagayama

  DOI：10.1016/j.bmcl.2017.09.028

  日期：2017.11

  Novel thienopyrimidine compounds 2 and 3 were discovered from high-throughput screening as Natriuretic Peptide Receptor A (NPR-A) agonists. Scaffold hopping of a thienopyrimidine ring to a quinazoline ring, introduction of the basic functional group and optimization of the substituent on the 6-position of the benzene ring of quinazoline led to improved agonistic activity. We discovered compound 48, which showed potent agonistic activity for NPR-A with an EC50 value of 0.073 mu M, indicating 350-fold potency compared to the hit compound 3. (C) 2017 Elsevier Ltd. All rights reserved.