2-(2-methoxybenzyl)-1H-pyrrole | 79499-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-methoxybenzyl)-1H-pyrrole
• 英文别名: 2-(o-Methoxybenzyl)pyrrole；2-(2-Methoxy-benzyl)-1h-pyrrole；2-[(2-methoxyphenyl)methyl]-1H-pyrrole
• CAS: 79499-35-7
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: FVIOROBJXUURKY-UHFFFAOYSA-N

物化性质

• 沸点：
  313.1±22.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-methoxybenzyl)-1H-pyrrole 在 1,1'-双(二苯基膦)二茂铁 、 potassium tert-butylate 、 双氧水 、 palladium diacetate 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-(((1r,4r)-4-hydroxycyclohexyl)amino)-4-(2-(2-methoxybenzyl)-1H-pyrrol-1-yl)benzamide
  参考文献：
  名称：

  Transformation of the Non-Selective Aminocyclohexanol-Based Hsp90 Inhibitor into a Grp94-Seletive Scaffold

  摘要：

  Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan- inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests,similar to 440 nM affinity and >200-fold selectivity against cytosolic Hsp90 isoforms.

  DOI：

  10.1021/acschembio.6b00747
• 作为产物：
  描述：

  吡咯 、 2-甲氧基溴苄 在 甲基溴化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(2-methoxybenzyl)-1H-pyrrole
  参考文献：
  名称：

  Transformation of the Non-Selective Aminocyclohexanol-Based Hsp90 Inhibitor into a Grp94-Seletive Scaffold

  摘要：

  Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan- inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests,similar to 440 nM affinity and >200-fold selectivity against cytosolic Hsp90 isoforms.

  DOI：

  10.1021/acschembio.6b00747

文献信息

• [EN] GRP94 SELECTIVE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS SÉLECTIFS DE GRP94 ET LEURS UTILISATIONS
  申请人：UNIV KANSAS

  公开号：WO2018081814A1

  公开（公告）日：2018-05-03

  The present technology provides compounds according to Formula I or Formula III as well as compositions including such compounds useful for the treatment of metastatic cancer and/or glaucoma.

  目前的技术提供了根据公式I或公式III提供的化合物，以及包括这些化合物的组合物，用于治疗转移性癌症和/或青光眼。
• Grp94 selective inhibitors and uses thereof
  申请人：University of Kansas

  公开号：US10975030B2

  公开（公告）日：2021-04-13

  The present technology provides compounds according to Formula I or Formula III as well as compositions including such compounds useful for the treatment of metastatic cancer and/or glaucoma.

  本技术提供了根据式 I 或式 III 的化合物以及包括此类化合物的组合物，可用于治疗转移性癌症和/或青光眼。
• [EN] Z-TYPE SOLANONE, PREPARATION METHOD THEREFOR, AND USE<br/>[FR] SOLANONE DE TYPE Z, PROCÉDÉ DE PREPARATION ASSOCIÉ, ET UTILISATION<br/>[ZH] 一种(Z)型茄酮、其制备方法及用途
  申请人：CHINA TOBACCO YUNNAN IND CO LTD

  公开号：WO2021068530A1

  公开（公告）日：2021-04-15

  本发明公开了一种(Z)型茄酮，其立体结构式为 (I) 或 (II) ，其名称为：(S,Z)-5-异丙基-8-甲基-6,8-二烯-2-酮、或(R,Z)-5-异丙基-8-甲基-6,8-二烯-2-酮。本发明还公开了所述(Z)型茄酮的制备方法及用卷烟烟丝加香的用途。
• Tandem alkylation-reduction of 2-acylpyrroles. Convenient one-pot syntheses of 2-benzylpyrroles
  作者：Doris P. Schumacher、Stan S. Hall

  DOI：10.1021/jo00338a002

  日期：1981.12
• SCHUMACHER, D. P.;HALL, S. S., J. ORG. CHEM., 1981, 46, N 25, 5060-5064
  作者：SCHUMACHER, D. P.、HALL, S. S.

  DOI：——

  日期：——