ethyl 2-methyl-1-phenyl-1H-pyrrole-3-carboxylate | 80326-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 2-methyl-1-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 2-methyl-1-phenylpyrrole-3-carboxylate
• CAS: 80326-73-4
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: NMVBKKUWTKACPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-1-phenyl-1H-pyrrole-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.67h， 生成 5-bromo-2-bromomethyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  PYRROLO- AND THIAZOLO-PYRIDINE COMPOUNDS, AND METHODS OF USE THEREOF

  摘要：

  这项发明涉及一种能够调节缺氧诱导因子（HIF）稳定性和/或活性的新化合物。

  公开号：

  US20080004309A1
• 作为产物：
  描述：

  1-phenyl-2-methyl-4,5-dihydropyrrol-3-carboxylic acid ethyl ester 在 5,10,15,20-tetrakisphenylporphyrin 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以40%的产率得到ethyl 2-methyl-1-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  一种新的单线态氧反应

  摘要：

  摘要——观察到 1-芳基-2-甲基-4,5-二氢吡咯-3-羧酸乙酯（一种环状烯胺）脱氢得到1-芳基-2-甲基-吡咯-3-羧酸乙酯。在存在氧气和存在或不存在间四苯基卟啉 (TPP) 的情况下进行辐照。N-芳基环胺被证明是单线态氧敏化剂。

  DOI：

  10.1111/j.1751-1097.1997.tb01880.x

文献信息

• Synthesis of Multisubstituted Pyrroles from Doubly Activated Cyclopropanes Using an Iron-Mediated Oxidation Domino Reaction
  作者：Zhiguo Zhang、Wei Zhang、Junlong Li、Qingfeng Liu、Tongxin Liu、Guisheng Zhang

  DOI：10.1021/jo5018487

  日期：2014.11.21

  An alternative route has been developed for the construction of multisubstituted pyrrole derivatives from readily available, doubly activated cyclopropanes and anilines using an iron-mediated oxidation domino reaction (i.e., sequential ring-opening, cyclization, and dehydrogenation reactions). This reaction uses readily available reactants and is tolerant of a broad range of substrates, with the desired

  已经开发出了另一种途径，用于利用铁介导的氧化多米诺反应（即顺序开环，环化和脱氢反应），从容易获得的双活化环丙烷和苯胺构造多取代的吡咯衍生物。该反应使用容易获得的反应物，并能耐受多种底物，形成所需产物的产率高至优异。
• Pyrrolo- and Thiazolo-pyridine compounds, and methods of use thereof
  申请人：FibroGen, Inc.

  公开号：US07696223B2

  公开（公告）日：2010-04-13

  The present invention relates to novel compounds capable of modulating the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及能够调节缺氧诱导因子（HIF）稳定性和/或活性的新化合物。
• THIAZOLO-PYRIDINE COMPOUNDS AS HIF MODULATORS
  申请人：Fibrogen, Inc.

  公开号：EP3124489A1

  公开（公告）日：2017-02-01

  The present invention relates to novel compounds of formula I wherein: q is 0 or 1; • A is -S- and B is =N-; or • A is =N- and B is -S-; one of -A≃C(R6)- or -B≃C(R6)- is a double bond and the other is a single bond; R1 is selected from the group consisting of hydroxyl, alkoxy, substituted alkoxy, acyloxy, cycloalkoxy, substituted cycloalkoxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, heterocyclyloxy, substituted heterocyclyloxy, mercapto, thioether, sustituted alkylthio, arylsulfanyl, heteroarylsulfanyl, amino, substituted amino, acylamino, and aminoacyl; R2is selected from the group consisting of hydrogen, deuterium, and methyl; R3 is selected from the group consisting of hydrogen, deuterium, alkyl, and substituted alkyl; R4 is selected from the group consisting of hydrogen, alkyl, and substituted alkyl; and R5 and R6 are as defined in claim 1; capable of modulating the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及式 I 的新型化合物 其中 q 是 0 或 1； - A 是-S-，B 是＝N-；或 - A 是 =N-，B 是 -S-； -A≃C(R6)-或-B≃C(R6)-中的一个是双键，另一个是单键； R1 选自由羟基、烷氧基、取代的烷氧基、酰氧基、环烷氧基、取代的环烷氧基、芳氧基、取代的芳氧基、杂芳氧基、取代的杂芳氧基、杂环氧基、取代的杂环氧基、巯基、硫醚、取代的烷硫基、芳硫基、杂芳硫基、氨基、取代的氨基、酰氨基和氨基酰基组成的组； R2 选自氢、氘和甲基组成的组； R3 选自氢、氘、烷基和取代烷基组成的组； R4 选自由氢、烷基和取代烷基组成的组；以及 R5 和 R6 如权利要求 1 所定义； 能调节缺氧诱导因子（HIF）的稳定性和/或活性。
• Screening of a Custom-Designed Acid Fragment Library Identifies 1-Phenylpyrroles and 1-Phenylpyrrolidines as Inhibitors of Notum Carboxylesterase Activity
  作者：William Mahy、Mikesh Patel、David Steadman、Hannah L. Woodward、Benjamin N. Atkinson、Fredrik Svensson、Nicky J. Willis、Alister Flint、Dimitra Papatheodorou、Yuguang Zhao、Luca Vecchia、Reinis R. Ruza、James Hillier、Sarah Frew、Amy Monaghan、Artur Costa、Magda Bictash、Magnus W. Walter、E. Yvonne Jones、Paul V. Fish

  DOI：10.1021/acs.jmedchem.0c00660

  日期：2020.9.10

  The Wnt family of proteins are secreted signaling proteins that play key roles in regulating cellular functions. Recently, carboxylesterase Notum was shown to act as a negative regulator of Wnt signaling by mediating the removal of an essential palmitoleate. Here we disclose two new chemical scaffolds that inhibit Notum enzymatic activity. Our approach was to create a fragment library of 250 acids for screening against Notum in a biochemical assay followed by structure determination by X-ray crystallography. Twenty fragments were identified as hits for Notum inhibition, and 14 of these fragments were shown to bind in the palmitoleate pocket of Notum. Optimization of 1-phenylpyrrole 20, guided by structure-based drug design, identified 20z as the most potent compound from this series. Similarly, the optimization of 1-phenylpyrrolidine 8 gave acid 26. This work demonstrates that inhibition of Notum activity can be achieved by small, drug-like molecules possessing favorable in vitro ADME profiles.
• On the problem of regioselectivity in the 1,3-dipolar cycloaddition reaction of munchnones and sydnones with acetylenic dipolarophiles
  作者：Albert Padwa、Edward M. Burgess、Henry L. Gingrich、David M. Roush

  DOI：10.1021/jo00344a008

  日期：1982.2