3-(4-bromophenyl)-1-methylpyrrole | 22099-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-bromophenyl)-1-methylpyrrole
• CAS: 22099-21-4
• 化学式: C₁₁H₁₀BrN
• 分子量: 236.111
• InChiKey: JEGOZFVHJCFZQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-(2-(4-bromophenyl)-3-(dimethylamino)allylidene)-N-methylmethanaminium perchlorate 在 吡啶 、 sodium methylate 作用下， 反应 24.0h， 生成 3-(4-bromophenyl)-1-methylpyrrole
  参考文献：
  名称：

  Structure–activity relationships in the inhibition of monoamine oxidase B by 1-methyl-3-phenylpyrroles

  摘要：

  Methyl-3-phenyl-3-pyrrolines are structural analogues of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and like MPTP are selective substrates of monoamine oxidase B (MAO-B). As part of an ongoing investigation into the substrate properties of various 1-methyl-3-phenyl-3-pyrrolinyl derivatives, it is shown in the present study that their respective MAO-B catalyzed oxidation products act as reversible competitive inhibitors of the enzyme. The most potent inhibitor among the oxidation products considered was 1-methyl-3-(4-trifluoromethylphenyl)pyrrole with an enzyme-inhibitor dissociation constant (K-i value) of 1.30 mu M. The least potent inhibitor was found to be 1-methyl-3-phenylpyrrole with a K-i value of 118 mu M. The results of an SAR study established that the potency of MAO-B inhibition by the 1-methyl-3-phenylpyrrolyl derivatives examined here is dependent on the Taft steric parameter (E-s) and Swain-Lupton electronic constant (F) of the substituents attached to C-4 of the phenyl ring. Electron-withdrawing substituents with a large degree of steric bulkiness appear to enhance inhibition potency. Potency was also found to vary with the substituents at C-3, again with E-s and F being the principal substituent descriptors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.059

文献信息

• [EN] PYRROLO[3,2-C]PYRIDINE DERIVATIVES AS TLR INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLO[3,2-C]PYRIDINE COMME INHIBITEURS DE TLR
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2015088045A1

  公开（公告）日：2015-06-18

  The present invention provides a heterocyclic compound having a TLR7, TLR9, TLR7/8, TLR7/9 or TLR7/8/9 inhibitory action, which is useful as an agent for the prophylaxis or treatment of autoimmune diseases, inflammatory diseases and the like, in particular, systemic lupus erythematosus, Sjogren's syndrome, rheumatoid arthritis, psoriasis, inflammatory bowel disease and the like. The present invention is a compound represented by the formula (1): wherein each symbol is as described in the specification, or a salt thereof.

  本发明提供了一种具有TLR7、TLR9、TLR7/8、TLR7/9或TLR7/8/9抑制作用的杂环化合物，该化合物可用作自身免疫性疾病、炎症性疾病等的预防或治疗剂，特别是系统性红斑狼疮、干燥综合征、类风湿关节炎、牛皮癣、炎症性肠病等。本发明是由式（1）表示的化合物：其中每个符号如说明书中所述，或其盐。
• β-Selective C–H Arylation of Pyrroles Leading to Concise Syntheses of Lamellarins C and I
  作者：Kirika Ueda、Kazuma Amaike、Richard M. Maceiczyk、Kenichiro Itami、Junichiro Yamaguchi

  DOI：10.1021/ja508449y

  日期：2014.9.24

  The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C

  吡咯的第一个通用 β 选择性 CH 芳基化已通过使用铑催化剂开发。这种 CH 芳基化反应在逆向合成上很简单，但会产生不寻常的区域选择性，可以从头合成吡咯衍生的天然产物和药物。因此，我们通过使用吡咯与芳基碘化物的这种β-选择性芳基化（CH / Cl 偶联）和新的双 CH / CH 偶联作为关键步骤，成功合成了多环海洋吡咯生物碱、层状菌素 C 和 I。
• Carbazole-based compound and organic light-emitting diode comprising the same
  申请人：Samsung Display Co., Ltd.

  公开号：EP2554545A1

  公开（公告）日：2013-02-06

  A carbazole-based compound of Formula 1 and an organic light-emitting diode including the same. The carbazole-based compound represented by Formula 1 has a triarylamine structure, wherein at least one of R1 to R5 is essentially a nitrogen-containing group. Thus, the carbazole-based compound has high glass transition temperature and/or high melting point, and is stable during electron injection, and when interposed between a pair of electrodes (anode and cathode) of an organic light-emitting diode, the carbazole-based compound may have excellent thermal resistance against Joule's heat generated in organic layers between the pair of electrodes, between the organic layers, or between the organic layer and the electrode during an operation of the organic light-emitting diode.

  一种式 1 的咔唑基化合物和包括该化合物的有机发光二极管。式 1 所代表的咔唑基化合物具有三芳基胺结构，其中 R1 至 R5 中至少有一个基本上是含氮基团。因此，咔唑基化合物具有较高的玻璃化温度和/或较高的熔点，在电子注入过程中稳定，而且当置于有机发光二极管的一对电极（阳极和阴极）之间时，咔唑基化合物对有机发光二极管工作期间在一对电极之间、有机层之间或有机层与电极之间的有机层中产生的焦耳热具有优异的耐热性。
• Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners
  作者：Rongwei Jin、Kedong Yuan、Emmanuelle Chatelain、Jean-François Soulé、Henri Doucet

  DOI：10.1002/adsc.201400736

  日期：2014.12.15

  AbstractThe reactivity of pyrrole derivatives for palladium‐catalysed desulfitative arylation has been investigated. 1‐Methyl‐, 1‐phenyl‐ and 1‐benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine‐free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated.It should be noted that even bromo‐ and iodo‐benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the CBr or CI bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2‐ and C3‐arylation products were obtained.magnified image
• Gallagher, Peter T.; Palmer, Jane L.; Morgan, Sarah E., Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3212 - 3214
  作者：Gallagher, Peter T.、Palmer, Jane L.、Morgan, Sarah E.

  DOI：——

  日期：——