methyl 2-phenyl-4-benzoxazolecarboxylate | 128156-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-phenyl-4-benzoxazolecarboxylate
• 英文别名: methyl 2-phenylbenzoxazole-4-carboxylate；methyl 2-phenyl-1,3-benzoxazole-4-carboxylate
• CAS: 128156-57-0
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: RVGQBABONQZPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-phenyl-4-benzoxazolecarboxylate 在 sodium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Critical structural motif for the catalytic inhibition of human topoisomerase II by UK-1 and analogs

  摘要：

  Three new analogs of UK-1 have been synthesized and their efficacies as topoisomerase II inhibitors have been determined. Results show that UK-1 and two of these analogs are catalytic inhibitors of topo II and identifies a critical structural motif necessary for enzyme inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.095
• 作为产物：
  描述：

  2-phenylbenzo[d]oxazole-4-carboxylic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 苯 为溶剂， 生成 methyl 2-phenyl-4-benzoxazolecarboxylate
  参考文献：
  名称：

  苯并恶唑作为运甲状腺素蛋白淀粉样蛋白原纤维抑制剂：合成，评估和作用机理。

  摘要：

  DOI：

  10.1002/anie.200351179

文献信息

• Benzamide analogs useful as PARP (ADP-ribosyltransferase, ADPRT) DNA
  申请人：Newcastle University Ventures Limited

  公开号：US05756510A1

  公开（公告）日：1998-05-26

  A range of 3-oxybenzamide compounds and related quinazolinone compounds are disclosed which can act as potent inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase or PARP enzyme (EC 2.4.2.30), and which thereby can provide useful therapeutic compounds for use in conjunction with DNA-damaging cytotoxic drugs or radiotherapy to potentiate the effects of the latter. The compounds disclosed include 3-benzyloxybenzamides, 3-oxybenzamides in which a chain of 5 or more methylene groups terminate in a halogen atom or in a purin-9-yl moiety, certain benzoxazole-4-carboxamide compounds and certain quinazolinone compounds. In formula X and Y together may form a bride --X--Y-- that represents the grouping (a), (b) or (c )wherein R.sup.5 is H, alkyl, aryl or aralkyl.

  揭示了一系列3-氧苯甲酰胺化合物和相关的喹唑啉酮化合物，它们可以作为DNA修复酶聚(ADP-核糖)聚合酶或PARP酶（EC 2.4.2.30）的有效抑制剂，并且因此可以提供用于与损伤DNA的细胞毒性药物或放疗结合使用以增强后者效果的有用治疗化合物。所披露的化合物包括3-苄氧基苯甲酰胺、3-氧基苯甲酰胺，其中5个或更多亚甲基基团的链以卤原子或吡嗪-9-基团结尾，某些苯并噁唑-4-甲酰胺化合物和某些喹唑啉酮化合物。在公式X和Y中，X和Y一起可以形成代表基团(a)、(b)或(c)的桥--X--Y--，其中R.sup.5为H、烷基、芳基或芳基烷基。
• Benzoxazole-4-carboxamides and their use in inhibiting poly (adp-ribose)
  申请人：Newcastle University Ventures Limited

  公开号：US06015827A1

  公开（公告）日：2000-01-18

  Benzoxazole carboxamides are disclosed which can act as potent inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase or PARP enzyme (EC 2.4.2.30), and which thereby can provide useful therapeutic compounds for use in conjunction with DNA-damaging cytotoxic drugs or radiotherapy to potentiate the effects of the latter. Representative of the compounds are 2-methyl, 2-t-butyl, 2-phenyl or 2-(4-methoxyphenyl) benzoxazole-4-carboxamide.

  本文披露了苯并噁唑羧酰胺，可作为DNA修复酶聚(ADP核糖)聚合酶或PARP酶(EC 2.4.2.30)的有效抑制剂，从而可提供有用的治疗化合物，用于与破坏DNA的细胞毒性药物或放疗结合使用，以增强后者的效果。该化合物的代表是2-甲基、2-t-丁基、2-苯基或2-(4-甲氧基苯基)苯并噁唑-4-羧酰胺。
• Method of improving the effectiveness of a cytotoxic drug or radiotherapy using a quinazolinone compound
  申请人：Newcastle University Ventures Limited

  公开号：US06316455B1

  公开（公告）日：2001-11-13

  A range of 3-oxybenzamide compounds and related quinazolinone compounds are disclosed which can act as potent inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase or PARP enzyme (EC 2.4.2.30), and which thereby can provide useful therapeutic compounds for use in conjunction with DNA-damaging cytotoxic drugs or radiotherapy to potentiate the effects of the latter. The coumpounds disclosed include 3-benzyloxybenzamides, 3-oxybenzamides in which a chain of 5 or more methylene groups terminate in a halogen atom or in a purin-9-yl moiety, certain benzoxazole-4-carboxamide compounds and certain quinazolinone compounds. In formula X and Y together may form a bride —X—Y— that represents the grouping (a), (b) or (c) wherein R5 is H, alkyl, aryl or aralkyl.

  本文披露了一系列3-氧基苯甲酰胺化合物和相关的喹唑啉酮化合物，可作为DNA修复酶聚(ADP-核糖)聚合酶或PARP酶（EC 2.4.2.30）的强效抑制剂，并因此可提供有用的治疗化合物，用于与DNA损伤细胞毒性药物或放疗结合使用，以增强后者的效果。披露的化合物包括3-苄氧基苯甲酰胺、3-氧基苯甲酰胺，其中5个或更多亚甲基基团的链以卤素原子或嘌呤-9-基团为终止基团，某些苯并噁唑-4-羧酰胺化合物和某些喹唑啉酮化合物。在公式X和Y中，它们可以组成一个桥-X-Y-，表示基团（a）、（b）或（c），其中R5为H，烷基，芳基或芳烷基。
• Extending the Scope of Chromium−Manganese Redox-Coupled Reactions:  A One-Pot Synthesis of Benzoxazoles
  作者：Anitha Hari、Charles Karan、Warren C. Rodrigues、Benjamin L. Miller

  DOI：10.1021/jo005758f

  日期：2001.2.1

  A critically important strategy for synthetic chemistry is the development of "domino" processes: those capable of concatenating multiple transformations into a single step. Such transformations not only provide an increase in synthetic efficiency, but also imply the development of a significant degree of mechanistic understanding. We report herein a new domino reaction, in which a chromium-manganese redox couple is employed both to catalytically reduce an o-hydroxy nitroarene and to oxidatively cyclize a subsequently formed imine. We find that the reaction is most effective for starting o-hydroxy nitroarenes with a strongly electron-withdrawing group at the para position.
• Goldstein, Steven W.; Dambeck, Paul J., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 335 - 336
  作者：Goldstein, Steven W.、Dambeck, Paul J.

  DOI：——

  日期：——