ethyl 4-hydroxy-2-oxo-4-(pyridin-2-yl)but-3-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-hydroxy-2-oxo-4-(pyridin-2-yl)but-3-enoate
• 英文别名: Ethyl 2-hydroxy-4-oxo-4-(pyridin-2-yl)but-2-enoate；ethyl 4-hydroxy-2-oxo-4-pyridin-2-ylbut-3-enoate
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: CKWHPTZNPGPUPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-2-oxo-4-(pyridin-2-yl)but-3-enoate 、 3-氯苯甲醛 、 甲胺 以 四氢呋喃 为溶剂， 反应 0.17h， 以77%的产率得到5-(3-chlorophenyl)-3-hydroxy-1-methyl-4-picolinoyl-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Rational design of 2-pyrrolinones as inhibitors of HIV-1 integrase

  摘要：

  HIV-1 integrase is an essential enzyme for viral replication and a validated target for the development of drugs against AIDS. With an aim to discover new potent inhibitors of HIV-1 integrase, we developed a pharmacophore model based on reported inhibitors embodying structural diversity. Eight compounds of 2-pyrrolinones fitting all the features of the pharmacophore query were found through the screening of an in-house database. These candidates were successfully synthesized, and three of them showed strand transfer inhibitory activity, in which, one compound showed antiviral activity. Further mapping analysis and docking studies affirmed these results. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.054
• 作为产物：
  描述：

  2-乙酰基吡啶 、 草酸二乙酯 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 以77%的产率得到ethyl 4-hydroxy-2-oxo-4-(pyridin-2-yl)but-3-enoate
  参考文献：
  名称：

  Rational design of 2-pyrrolinones as inhibitors of HIV-1 integrase

  摘要：

  HIV-1 integrase is an essential enzyme for viral replication and a validated target for the development of drugs against AIDS. With an aim to discover new potent inhibitors of HIV-1 integrase, we developed a pharmacophore model based on reported inhibitors embodying structural diversity. Eight compounds of 2-pyrrolinones fitting all the features of the pharmacophore query were found through the screening of an in-house database. These candidates were successfully synthesized, and three of them showed strand transfer inhibitory activity, in which, one compound showed antiviral activity. Further mapping analysis and docking studies affirmed these results. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.054

文献信息

• [EN] NITROGEN-CONTAINING HETEROARYL DERIVATIVES<br/>[FR] DÉRIVÉS HÉTÉROARYLIQUES CONTENANT DE L'AZOTE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011089132A1

  公开（公告）日：2011-07-28

  The invention is concerned with novel nitrogen-containing heteroaryl derivatives of formula (I) wherein R1, R2, R3, R4, R5, A1, A2, and Y are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as medicaments.

  本发明涉及式(I)的新氮杂芳基衍生物，其中R1、R2、R3、R4、R5、A1、A2和Y的定义如描述和权利要求中所述，以及这些化合物的生理可接受的盐和酯。这些化合物可以抑制PDE10A，并可作为药物使用。
• NITROGEN-CONTAINING HETEROARYL DERIVATIVES
  申请人：Bleicher Konrad

  公开号：US20110183979A1

  公开（公告）日：2011-07-28

  The invention is concerned with novel nitrogen-containing heteroaryl derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , A 1 , A 2 , and Y are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as medicaments.

  本发明涉及式(I)的新氮杂芳基衍生物，其中R1、R2、R3、R4、R5、A1、A2和Y的定义如描述和权利要求中所述，以及这些化合物的生理可接受的盐和酯。这些化合物可以抑制PDE10A，并可作为药物使用。
• US8470820B2
  申请人：——

  公开号：US8470820B2

  公开（公告）日：2013-06-25
• Rational design of 2-pyrrolinones as inhibitors of HIV-1 integrase
  作者：Kaiqing Ma、Penghui Wang、Wei Fu、Xiaolong Wan、Lu Zhou、Yong Chu、Deyong Ye

  DOI：10.1016/j.bmcl.2011.09.054

  日期：2011.11

  HIV-1 integrase is an essential enzyme for viral replication and a validated target for the development of drugs against AIDS. With an aim to discover new potent inhibitors of HIV-1 integrase, we developed a pharmacophore model based on reported inhibitors embodying structural diversity. Eight compounds of 2-pyrrolinones fitting all the features of the pharmacophore query were found through the screening of an in-house database. These candidates were successfully synthesized, and three of them showed strand transfer inhibitory activity, in which, one compound showed antiviral activity. Further mapping analysis and docking studies affirmed these results. (C) 2011 Elsevier Ltd. All rights reserved.