ethyl 3-amino-5-(phenylmethyl)-2-pyridinecarboxylate | 675616-28-1

• 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: ethyl 3-amino-5-(phenylmethyl)-2-pyridinecarboxylate
• 英文别名: ethyl 3-amino-5-benzylpyridine-2-carboxylate
• CAS: 675616-28-1
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: PXMJVGXJMOWKGR-UHFFFAOYSA-N

物化性质

• 熔点：
  119-122 °C
• 沸点：
  454.8±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-5-(phenylmethyl)-2-pyridinecarboxylate 在 dimethyl sulfide borane 、 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Combining symmetry elements results in potent naphthyridinone (NTD) HIV-1 integrase inhibitors

  摘要：

  A series of naphthyridinone HIV-1 integrase strand-transfer inhibitors have been designed based on a psdeudo-C2 symmetry element present in the two-metal chelation pharmacophore. A combination of two distinct inhibitor binding modes resulted in potent inhibition of the integrase strand-transfer reaction in the low nM range. Effects of aryl and N1 substitutions are disclosed including the impact on protein binding adjusted antiviral activity. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.08.082
• 作为产物：
  描述：

  Ethyl 5-benzyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以8.7 g的产率得到ethyl 3-amino-5-(phenylmethyl)-2-pyridinecarboxylate
  参考文献：
  名称：

  Synthesis and Antiviral Activity of 7-Benzyl-4-hydroxy-1,5-naphthyridin-2(1H)-one HIV Integrase Inhibitors

  摘要：

  The medicinal chemistry and structure-activity relationships for a novel series of 7-benzyl-4-hydroxy-1,5-naphthyridin-2(1H)-one HIV-integrase inhibitors are disclosed. Substituent effects were evaluated at the N-1, C-3, and 7-benzyl positions of the naphthyridinone ring system. Low nanomolar IC50 values were achieved in an HIV-integrase strand transfer assay with both carboxylic ester and carboxamide groups at C-3. More importantly, several carboxamide congeners showed potent antiviral activity in cellular assays. A 7-benzyl substituent was found to be critical for potent enzyme inhibition, and an N-(2-methoxyethyl)-carboxamide moiety at C-3 significantly reduced plasma protein binding effects in vitro. Pharmacokinetic data in rats for one carboxamide analogue demonstrated oral bioavailability and reasonable in vivo clearance.

  DOI：

  10.1021/jm801404b

文献信息

• HIV INTEGRASE INHIBITORS
  申请人：ViiV Healthcare Company

  公开号：US20150225399A1

  公开（公告）日：2015-08-13

  The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

  本发明具有作为HIV整合酶抑制剂的化合物，因此在抑制HIV复制、预防及/或治疗HIV感染以及治疗艾滋病及/或艾滋病相关综合症方面具有用途。
• Hiv Integrase Inhibitors
  申请人：Johns Alvin Brian

  公开号：US20070124152A1

  公开（公告）日：2007-05-31

  The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

  本发明涉及一种HIV整合酶抑制剂化合物，因此在抑制HIV复制，预防和/或治疗HIV感染以及治疗艾滋病和/或ARC方面具有用途。
• Heterocyclic compounds having inhibitory activity against HIV integrase
  申请人：Murai Hitoshi

  公开号：US20090118233A1

  公开（公告）日：2009-05-07

  A heterocyclic compound of the formula (I): wherein B 1 is —C(R 2 )═ or —N═; R 1′ is H, etc.; one of R 1 and R 2 is -Z 1 -Z 2 -Z 3 -R 5 wherein Z 1 and Z 3 are independently single bond, optionally substituted alkylene, etc.; Z 2 is single bond, optionally substituted alkylene, etc.; R 5 is optionally substituted aryl, optionally substituted heteroaryl, etc., and the other of R 1 and R 2 is H; -A 1 - is —C(—Y)═C(—R A )—C(—R 3 )═C(—R 4 )—, etc. wherein Y is OH, etc.; R A is —COR 7 wherein R 7 is OH, etc.; one of R 3 and R 4 is carboxy, etc., and the other of R 1 and R 2 is H, etc, a prodrug thereof, a pharmaceutically acceptable salt thereof, and a solvate thereof, having an antiviral activity, more particularly, an inhibitory activity against HIV integrase, and a pharmaceutical composition containing the same, especially an anti-HIV drug.

  一种具有以下式（I）的杂环化合物：其中B1为—C（R2）═或—N═；R1'为H等；R1和R2中的一个为-Z1-Z2-Z3-R5，其中Z1和Z3分别为单键，可选择性地取代的烷基等；Z2为单键，可选择性地取代的烷基等；R5为可选择性取代的芳基，可选择性取代的杂环芳基等；R1和R2中的另一个为H；-A1-为—C（—Y）═C（—RA）—C（—R3）═C（—R4）—等，其中Y为OH等；RA为—COR7，其中R7为OH等；R3和R4中的一个为羧基等，另一个为H等。该化合物的前药、其药学上可接受的盐和溶剂化物具有抗病毒活性，尤其是对HIV整合酶的抑制活性，并且包含该化合物的药物组合物，特别是一种抗HIV药物。
• 2-oxonaphthyridine-3-carboxamides HIV integrase inhibitors
  申请人：Johns Brian Alvin

  公开号：US08691991B2

  公开（公告）日：2014-04-08

  The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

  本发明涉及能够抑制HIV整合酶的化合物，因此可用于抑制HIV复制，预防和/或治疗HIV感染，以及治疗艾滋病和/或ARC。
• US20140256713A1
  申请人：——

  公开号：——

  公开（公告）日：——