4-苯甲酰基-1H-吡咯-2-羧酸甲酯 | 34628-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-苯甲酰基-1H-吡咯-2-羧酸甲酯
• 英文名称: methyl 4-benzoyl 1H-pyrrole-2-carboxylate
• 英文别名: Methyl 4-benzoyl-1H-pyrrole-2-carboxylate
• CAS: 34628-36-9
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: BIDNYJAGIABSOW-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151°C
• 沸点：
  426.6±30.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-苯甲酰基-1H-吡咯-2-羧酸甲酯 在 sodium tetrahydroborate 、 对甲苯磺酸 、 溶剂黄146 、 对甲苯磺酰肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 4-benzyl-5-[1-(3-benzyl-5-methoxycarbonyl-1H-pyrrol-2-yl)butyl]-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Modular Preparation of Diverse Dipyrrolemethanes

  摘要：

  A modular synthesis of polyfunctional dipyrrolemethanes is presented. Diverse side chains are introduced to 2-carboxypyrrole building blocks in two to four steps, resulting in a collection of substituted pyrroles that, when condensed in one step, give rise to diverse structural features.

  DOI：

  10.1055/s-0032-1318503
• 作为产物：
  描述：

  3-苯-1-丙炔 、 异腈基乙酸甲酯 在 nano-copper⁽⁰⁾ stabilized on alumina 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以67%的产率得到4-苯甲酰基-1H-吡咯-2-羧酸甲酯
  参考文献：
  名称：

  Nano-copper catalysed highly regioselective synthesis of 2,4-disubstituted pyrroles from terminal alkynes and isocyanides

  摘要：

  从Cu-Al水滑石制备的氧化铝上稳定的纳米铜(0)已被报道用于从未活化的末端芳香/脂肪炔烃和异氰酸酯完全区域选择性合成2,4-二取代吡咯。

  DOI：

  10.1039/c5cc04166j

文献信息

• Catalytic Chemo- and Regioselective Coupling of 1,3-Dicarbonyls with <i>N</i>-Heterocyclic Nucleophiles
  作者：Miles Kenny、Daniel J. Kitson、Vilius Franckevičius

  DOI：10.1021/acs.joc.6b00731

  日期：2016.6.17

  compounds with indole, pyrrole, imidazole, and pyrazole nucleophiles via an allylic linker under neutral conditions is disclosed. This process enables the installation of an all-carbon quaternary center and new C–C and C–N bonds in a single operation. Despite the weakly acidic nature of N-heterocycles, the reactions proceed with good efficiency and complete regio- and chemoselectivity.

  公开了在中性条件下经由烯丙基连接体开发的脱羧钯催化的1，3-二羰基化合物与吲哚，吡咯，咪唑和吡唑亲核试剂的偶联。此过程可在一次操作中安装全碳四元中心以及新的C–C和C–N键。尽管N-杂环具有弱酸性，但反应仍能高效进行，并具有完全的区域选择性和化学选择性。
• High-Throughput Screening and Hit Validation of Extracellular-Related Kinase 5 (ERK5) Inhibitors
  作者：Stephanie M. Myers、Ruth H. Bawn、Louise C. Bisset、Timothy J. Blackburn、Betty Cottyn、Lauren Molyneux、Ai-Ching Wong、Celine Cano、William Clegg、Ross. W. Harrington、Hing Leung、Laurent Rigoreau、Sandrine Vidot、Bernard T. Golding、Roger J. Griffin、Tim Hammonds、David R. Newell、Ian R. Hardcastle

  DOI：10.1021/acscombsci.5b00155

  日期：2016.8.8

  The extracellular-related kinase 5 (ERK5) is a promising target for cancer therapy. A high-throughput screen was developed for ERK5, based on the IMAP FP progressive binding system, and used to identify hits from a library of 57 617 compounds. Four distinct chemical series were evident within the screening hits. Resynthesis and reassay of the hits demonstrated that one series did not return active

  细胞外相关激酶5（ERK5）是癌症治疗的有希望的目标。基于IMAP FP渐进结合系统，针对ERK5开发了高通量筛选，并用于从57 617种化合物的文库中鉴定命中。筛选命中明显有四个不同的化学系列。命中的重新合成和重新测定表明，一个系列没有返回活性化合物，而三个系列返回了活性命中。结构活性研究表明，4-苯甲酰基吡咯-2-羧酰胺药效团具有很好的进一步开发潜力。鉴定了最小的激酶结合药效基团，关键实例证明了对ERK5的选择性优于p38α激酶。
• Pyrrole and pyrazole DAAO inhibitors
  申请人：Fang Kevin Q.

  公开号：US20050143443A1

  公开（公告）日：2005-06-30

  Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein R 1 and R 2 are independently selected from hydrogen, halo, nitro, alkyl, acyl, alkylaryl, and XYR 5 ; or R 1 and R 2 , taken together, form a 5, 6, 7 or 8-membered substituted or unsubstituted carbocyclic or heterocyclic group; X and Y are independently selected from O, S, NH, and (CR 6 R 7 ) n ; R 3 is hydrogen, alkyl or M + ; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc ion or a mixture thereof; Z is N or CR 4 ; R 4 is from selected from hydrogen, halo, nitro, alkyl, alkylaryl, and XYR 5 ; R 5 is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R 6 and R 7 are independently selected from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R 1 , R 2 and R 4 is other than hydrogen; and at least one of X and Y is (CR 6 R 7 ) n . D-serine or cycloserine may be coadministered along with the compound of formula I.

  增加D-丝氨酸浓度和减少D-丝氨酸氧化的有毒产物浓度的方法，用于增强学习、记忆和/或认知能力，或用于治疗精神分裂症、阿尔茨海默病、共济失调或神经病性疼痛，或预防神经元功能丧失，这涉及向需要治疗的受试者施用化合物I的治疗有效量，或其药学上可接受的盐或溶剂：其中R1和R2独立地选自氢、卤素、硝基、烷基、酰基、烷基芳基和XYR5；或R1和R2共同形成一个5、6、7或8-成员的取代或未取代的碳环或杂环基团；X和Y独立地选自O、S、NH和(CR6R7)n；R3为氢、烷基或M+；M为铝、钙、锂、镁、钾、钠、锌离子或其混合物；Z为N或CR4；R4选自氢、卤素、硝基、烷基、烷基芳基和XYR5；R5选自芳基、取代芳基、杂环芳基和取代杂环芳基；R6和R7独立地选自氢和烷基；n为1到6的整数；R1、R2和R4中至少有一个不是氢；X和Y中至少有一个是(CR6R7)n。 D-丝氨酸或环丝氨酸可以与化合物I的共同给药。
• Isoxazolo derivatives
  申请人：Buettelmann Bernd

  公开号：US20070066668A1

  公开（公告）日：2007-03-22

  The present invention is concerned with aryl-isoxazole-4-carbonyl-pyrrole-2-carboxylic acid amide derivatives of formula wherein R 1 , R 2 , R 3 , R 4 , and R 5 , and m are as defined herein and with their pharmaceutically acceptable acid addition salts. This class of compounds have high affinity and selectivity for GABA A α5 receptor binding sites and therefore may be useful as cognitive enhancer or for the treatment of cognitive disorders like Alzheimer's disease.

  本发明涉及一种芳基异噁唑-4-甲酰基-吡咯-2-羧酸酰胺衍生物，其化学式为其中R1、R2、R3、R4和R5以及m的定义如本文所述，并且涉及它们的药学上可接受的酸盐。这类化合物具有高亲和力和选择性，可结合到GABA A α5受体结合位点，因此可能用作认知增强剂或用于治疗像阿尔茨海默病这样的认知障碍。
• The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents
  作者：Maria E. Chizhova、Dmitry V. Dar’in、Mikhail Krasavin

  DOI：10.1016/j.mencom.2020.07.030

  日期：2020.7

  Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from

  在Castagnoli-Cushman与亚胺的反应中，已经研究了在双环系统的6或7位带有吸电子取代基的1-（羧甲基）吡咯-2-羧酸的四种酸酐。6-苯甲酰基-和7-氨磺酰基取代的酸酐显示出较低的反应性，而7-苯甲酰基衍生物显示出较宽的底物范围。这些发现已从机制的角度进行了合理化。