3-amino-4-phenylbut-2-enoic acid ethyl ester | 960298-94-6

• 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: 3-amino-4-phenylbut-2-enoic acid ethyl ester
• 英文别名: (E)-ethyl 3-amino-4-phenylbut-2-enoate；ethyl (E)-3-amino-4-phenylbut-2-enoate
• CAS: 960298-94-6
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: YNUYZZJNYFATIM-PKNBQFBNSA-N

物化性质

• 沸点：
  353.4±37.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4-phenylbut-2-enoic acid ethyl ester 在 原甲酸三乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 ethyl 4-benzyl-1-(4-(benzyloxy)phenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  WO2007/146824

  摘要：

  公开号：
• 作为产物：
  描述：

  4-苯基乙酰乙酸乙酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3-amino-4-phenylbut-2-enoic acid ethyl ester
  参考文献：
  名称：

  Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener

  摘要：

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

  DOI：

  10.1021/jm060549u

文献信息

• Sonochemical synthesis of 2-substituted nicotinic acid ethyl ester derivatives: Their in vitro and in silico evaluation against SIRT1
  作者：Chandra Sekhar Challa、Naresh Kumar Katari、Varadacharyulu Nallanchakravarthula、Devanna Nayakanti、Ravikumar Kapavarapu、Manojit Pal

  DOI：10.1016/j.molstruc.2021.131069

  日期：2021.12

  potential of 2-substituted nicotinic acid ethyl ester derivatives was undertaken in vitro. A sonochemical method was developed and employed for the faster synthesis of this class of compounds. The methodology involved the iodine-mediated reaction of β-enamino esters with allylic alcohols in aqueous DMSO in the presence of air under mild conditions. A number of 2-substituted nicotinic acid ethyl ester

  基于有代表性的化合物的初始对接研究在硅片2-取代烟酸乙酯衍生物的SIRT1抑制潜力的评价进行体外。开发并采用了一种声化学方法来更快地合成此类化合物。该方法涉及碘介导的β反应-烯氨基酯与烯丙醇在 DMSO 水溶液中，在温和条件下，在空气存在下。使用这种超声辅助方法合成了许多 2-取代的烟酸乙酯衍生物，产率达到可接受的水平。使用较便宜的碘和水介质、更温和的反应条件和更短的反应时间是当前方法的主要优点。所有合成的化合物在体外测试了它们的SIRT1抑制潜力，当其中一些表现出良好的活性时，化合物3g是其中最好的。对接研究表明，3g的稠合内酯环在与 SIRT1的硅相互作用中起关键作用，通过氢键的形成。体外和计算机研究的总体结果表明，化合物3g是进一步药理学研究的初始命中分子。
• QUINOLINE COMPOUNDS AND METHODS OF USE
  申请人：Gaudino John

  公开号：US20110053931A1

  公开（公告）日：2011-03-03

  Compounds of Formula (I), and stereoisomers, geometric isomers, tautomers, solvates, metabolites, salts and pharmaceutically acceptable prodrugs thereof, are useful for inhibiting receptor tyrosine kinases and for treating hyperproliferative disorders mediated thereby. Methods of using compounds of Formula (I), and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  式（I）的化合物及其立体异构体、几何异构体、互变异构体、溶剂化物、代谢物、盐和药学上可接受的前药，用于抑制受体酪氨酸激酶并治疗由此介导的过度增殖性疾病。本文揭示了使用式（I）的化合物及其立体异构体、几何异构体、互变异构体、溶剂化物和药学上可接受的盐，在哺乳动物细胞中进行体外、体内和原位诊断、预防或治疗此类疾病或相关病理条件的方法。
• OKA Y.; OMURA K.; MIYAKE A.; ITOH K.; TOMIMOTO M.; TADA N.; YURUGI S., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 10, 2239-2250
  作者：OKA Y.、 OMURA K.、 MIYAKE A.、 ITOH K.、 TOMIMOTO M.、 TADA N.、 YURUGI S.

  DOI：——

  日期：——
• WO2007/146824
  申请人：——

  公开号：——

  公开（公告）日：——
• Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3<i>H</i>,4<i>H</i>-2,6-dioxa-4- azacyclopenta[<i>b</i>]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener
  作者：Robert J. Altenbach、Michael E. Brune、Steven A. Buckner、Michael J. Coghlan、Anthony V. Daza、Adebola Fabiyi、Murali Gopalakrishnan、Rodger F. Henry、Albert Khilevich、Michael E. Kort、Ivan Milicic、Victoria E. Scott、Jamie C. Smith、Kristi L. Whiteaker、William A. Carroll

  DOI：10.1021/jm060549u

  日期：2006.11.1

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.