3-phenyl-2,7-naphthyridin-1(2H)-one | 92905-81-2

• 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: 3-phenyl-2,7-naphthyridin-1(2H)-one
• 英文别名: 3-phenyl-2,7-naphthyridin-1-one；3-phenyl-2H-[2,7]naphthyridin-1-one；3-Phenyl-2H-[2,7]naphthyridin-1-on；1-Oxo-3-phenyl-1,2-dihydro-copyrin；3-phenyl-2H-2,7-naphthyridin-1-one
• CAS: 92905-81-2
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: MHEBYJLLLNVBQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  499.6±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-2,7-naphthyridin-1(2H)-one 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以11%的产率得到2-methyl-8-oxo-6-phenyl-2,7-naphthyridin-2-ium iodide
  参考文献：
  名称：

  Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

  摘要：

  The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl) ate their target proteins using NAD(+) as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with beta-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d] pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused > 1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.005
• 作为产物：
  描述：

  7-benzyl-3-phenyl-2,7-naphthyridin-1(7H)-one 在 甲酸 、 palladium on carbon 、 甲酸铵 作用下， 以 四氢呋喃 为溶剂， 以91 mg的产率得到3-phenyl-2,7-naphthyridin-1(2H)-one
  参考文献：
  名称：

  通过Reissert反应/分子内亲核加成/氧化脱氢串联合成取代的2,7-萘啶-1（7 H）-

  摘要：

  已经开发了一种方便的合成取代的2,7-萘啶-1（7 H）-的方法。该方法从简单的烟酰胺盐开始，通过串联过程进行，包括Reissert反应，分子内亲核加成和氧化脱氢。使用该方法，以高收率获得了各种取代的2,7-萘啶-1（7 H）-。

  DOI：

  10.1016/j.tet.2013.05.105

文献信息

• [EN] TANKYRASE INHIBITORS<br/>[FR] INHIBITEURS DE TANKYRASE
  申请人：UNIV BATH

  公开号：WO2014087165A1

  公开（公告）日：2014-06-12

  The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.

  本发明涉及一种具有式I的化合物，其中X为C(R6)或N，Y为C或N，环A、环B、R1和R2具有本文中定义的含义，前提是当环B为碳环时，X为C(R6)；或其药学上可接受的盐或溶剂。这些化合物是坦克酶-1和坦克酶-2抑制剂，并可用于治疗多种疾病，包括癌症。
• 3-Substituted 2,7-naphthyridin-1-yl derivatives
  申请人：——

  公开号：US20020137935A1

  公开（公告）日：2002-09-26

  3-Substituted 2,7-naphthyridine derivatives of formula (1) are described: 1 wherein L 1 and L 1 is each a covalent bond or a linker atom or group; Alk 1 is an optionally substituted aliphatic chain; R 2 is a hydrogen atom or an optionally substitued heteroaliphatic, cycloaliphatic, heterocycloaliphatic, polycycloaliphatic, heteropolycycloaliphatic, aromatic or heteroaromatic group; 2 in which R is a carboxylic acid (—CO 2 H) or a derivative or biostere thereof; Ar 2 is an optionally substituted aromatic or heteroaromatic linking group; R 16 is the group -L 3 (Alk 2 ) t L 4 R 20 in which L 3 and L 4 which may be the same or different is each a covalent bond or a linker atom or group, t is zero or the integer 1, Alk 2 is an optionally substituted aliphatic or heteroaliphatic chain and R 20 is an optionally substituted aromatic or heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immuno or inflammatory disorders or disorders involving the inappropriate growth or migration of cells.

  描述了式（1）的3-取代2,7-萘啶衍生物：1其中L1和L2分别是共价键或连接原子或基团；Alk1是可选的取代脂肪链；R2是氢原子或可选的取代杂脂肪、环状脂肪、杂环状脂肪、多环状脂肪、杂多环状脂肪、芳香或杂芳基团；其中R是羧酸（-CO2H）或其衍生物或生物立体异构体；Ar2是可选的取代芳香或杂芳香连接基团；R16是-L3（Alk2）tL4R20基团，其中L3和L4可以相同也可以不同，分别是共价键或连接原子或基团，t为零或整数1，Alk2是可选的取代脂肪或杂脂肪链，R20是可选的取代芳香或杂芳基团；以及其盐、溶剂化物、水合物和N-氧化物。这些化合物能够抑制整合素与其配体的结合，并用于预防和治疗免疫或炎症性疾病或涉及细胞不适当生长或迁移的疾病。
• 3-substituted 2,7-naphthyridin-1-yl derivatives
  申请人：Celltech R&D Limited

  公开号：US06593338B2

  公开（公告）日：2003-07-15

  3-Substituted 2,7-naphthyridine derivatives of formula (1) are described: wherein L1 and L1 is each a covalent bond or a linker atom or group; Alk1 is an optionally substituted aliphatic chain; R2 is a hydrogen atom or an optionally substituted heteroaliphatic, cycloaliphatic, heterocycloaliphatic, polycycloaliphatic, heteropolycycloaliphatic, aromatic or heteroaromatic group; Alk is a chain in which R is a carboxylic acid (—CO2H) or a derivative or biostere thereof; Ar2 is an optionally substituted aromatic or heteroaromatic linking group; R16 is the group —L3(Alk2)tL4R20 in which L3 and L4 which may be the same or different is each a covalent bond or a linker atom or group, t is zero or the integer 1, Alk2 is an optionally substituted aliphatic or heteroaliphatic chain and R20 is an optionally substituted aromatic or heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immuno or inflammatory disorders or disorders involving the inappropriate growth or migration of cells.

  描述了式（1）的3-取代2,7-萘啶衍生物：其中L1和L1均为共价键或连接原子或基团；Alk1是可选取代的脂肪链；R2是氢原子或可选取代的杂脂肪、环状脂肪、杂环状脂肪、多环状脂肪、杂多环状脂肪、芳香或杂芳香基团；Alk是其中R为羧酸（-CO2H）或其衍生物或生物立体异构体的链；Ar2是可选取代的芳香或杂芳香连接基团；R16是-L3（Alk2）tL4R20基团，其中L3和L4可以相同也可以不同，均为共价键或连接原子或基团，t为零或整数1，Alk2是可选取代的脂肪或杂脂肪链，R20是可选取代的芳香或杂芳香基团；以及其盐、溶剂化物、水合物和N-氧化物。该化合物能够抑制整合素与其配体的结合，并可用于预防和治疗免疫或炎症性疾病或涉及细胞异常增长或迁移的疾病。
• Kroehnke et al., Justus Liebigs Annalen der Chemie, 1956, vol. 600, p. 176,188
  作者：Kroehnke et al.

  DOI：——

  日期：——
• 3-SUBSTITUTED 2,7-NAPHTHYRIDIN-1-YL DERIVATIVES
  申请人：Celltech R & D Limited

  公开号：EP1337534A1

  公开（公告）日：2003-08-27