6-氧代-5H-菲啶-3-羧酸 | 39161-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 6-氧代-5H-菲啶-3-羧酸
• 英文名称: 5[H]phenanthridin-6-one carboxylic acid
• 英文别名: 6-oxo-5,6-dihydro-phenanthridine-3-carboxylic acid；6-Phenanthridon-3-carbonsaeure；5,6-Dihydro-6-oxophenanthridine-3-carboxylic acid；6-oxo-5H-phenanthridine-3-carboxylic acid
• CAS: 39161-52-9
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: QCZYYHNRVZRTGW-UHFFFAOYSA-N

物化性质

• 沸点：
  389.4±21.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氧代-5H-菲啶-3-羧酸 在 盐酸 、 三乙胺 、 三氯氧磷 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-Phenyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-5H-phenanthridin-6-one; hydrochloride
  参考文献：
  名称：

  4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors

  摘要：

  We have shown that a 4-phenyl-1,2,3,6-tetrahydropyridine fragment plays an important role in improving inhibitory potency against poly(ADP-ribose) polymerise-1 (PARP-1). Various benzamide analogues linked with this fragment via alkyl spacers have been prepared and evaluated. As a result, some of them have been found to be highly potent PARP-1 inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.094
• 作为产物：
  描述：

  4-碘-3-硝基苯甲酸甲酯 在 sodium hydroxide 、 镍 、 铜 、 肼 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 6-氧代-5H-菲啶-3-羧酸
  参考文献：
  名称：

  Synthesis of substituted 5[H]phenanthridin-6-ones as potent poly(ADP-ribose)polymerase-1 (PARP1) inhibitors

  摘要：

  1-, 2-, 3-, 4-, 8-, or 10-Substituted 5(H)phenanthridin-6-ones were synthesized and found to be potent PARP1 inhibitors. Among the 28 compounds prepared. some showed not only low IC50 values (compound 1b, 10 nM) but also desirable water solubility characteristics. These properties, which are superior to the common PARP1 inhibitors such as benzamides and isoquinolin-1-ones, are essential for potential therapeutic usage. The variety of compounds allows SAR analysis of favored substituents and substituted positions on 5(H)phenanthridin-6-one ring. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00281-5

文献信息

• PROTEIN KINASE MODULATORS
  申请人：CHUA Peter C.

  公开号：US20090239859A1

  公开（公告）日：2009-09-24

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. Molecules of the invention can modulate Pim kinase activity and/or FMS-like tyrosine kinase (Flt) activity. The invention also relates in part to methods for using such molecules.

  该发明部分涉及具有特定生物活性的分子，包括但不限于抑制细胞增殖、调节蛋白激酶活性和调节聚合酶活性。该发明的分子可以调节Pim激酶活性和/或FMS样酪氨酸激酶（Flt）活性。该发明还涉及使用这些分子的方法。
• Phenanthridinones as parp inhibitors
  申请人：Yamamoto Hirofumi

  公开号：US20050171101A1

  公开（公告）日：2005-08-04

  A compound of the formula (I): wherein ring A is a carbocyclic group, R1 is hydrogen or a halogen atom or a lower alkyl group, R2 is a di(lower)alkylamino group or N-containing heterocyclic group, among which the N-containing heterocyclic group may be substituted with one or more substituent(s), Y is an oxygen or sulfur atom, n is an integer from 0 to 2, and m is an integer from 0 to 4, or its prodrug, or their salt which has poly(adenosine 5′-diphospho-ribose)polymerase inhibiting activity.

  化合物的式子(I)如下：其中环A是一个碳环基团，R1是氢原子或卤素原子或低碳基团，R2是二(低)烷基氨基团或含N的杂环基团，其中含N的杂环基团可以被一个或多个取代基取代，Y是氧原子或硫原子，n是0到2之间的整数，m是0到4之间的整数，或其前药，或其具有聚腺苷酸二磷酸核糖酶抑制活性的盐。
• SERINE-THREONINE PROTEIN KINASE AND PARP MODULATORS
  申请人：CHUA Peter

  公开号：US20090264423A2

  公开（公告）日：2009-10-22

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. Molecules of the invention can modulate casein kinase (CK) activity and/or poly(ADP-ribose)polymerase (PARP) activity. The invention also relates in part to methods for using such molecules.

  本发明涉及具有某些生物活性的分子，包括但不限于抑制细胞增殖、调节蛋白激酶活性和调节聚合酶活性。本发明的分子可以调节酪蛋白激酶（CK）活性和/或聚(ADP-核糖)聚合酶（PARP）活性。本发明还涉及使用这些分子的方法。
• FUSED TRICYCLIC COMPOUNDS AS SERINE-THREONINE PROTEIN KINASE AND PARP MODULATORS
  申请人：CHUA Peter C.

  公开号：US20110263581A1

  公开（公告）日：2011-10-27

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. Molecules of the invention can modulate casein kinase (CK) activity and/or poly(ADP-ribose)polymerase (PARP) activity. The invention also relates in part to methods for using such molecules.

  本发明部分涉及具有某些生物活性的分子，包括但不限于抑制细胞增殖、调节蛋白激酶活性和调节聚合酶活性。本发明的分子可以调节酪氨酸激酶（CK）活性和/或聚(ADP核糖)聚合酶（PARP）活性。本发明部分还涉及使用这些分子的方法。
• Woodroofe, Carolyn C.; Zhong, Boyu; Lu, Xingliang, Journal of the Chemical Society. Perkin transactions II, 2000, # 1, p. 55 - 60
  作者：Woodroofe, Carolyn C.、Zhong, Boyu、Lu, Xingliang、Silverman, Richard B.

  DOI：——

  日期：——