5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile
• 英文别名: 5-[4-amino-3-(2-hydroxypropan-2-yl)phenyl]-1-methylpyrrole-2-carbonitrile
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: AKWXTECOJTWHIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile 、 [¹¹C]carbon disulfide 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 [¹¹C]tanaproget
  参考文献：
  名称：

  [18F]氟甲基-Tanaproget衍生物的合成及其对孕酮受体表达成像的临床前评价

  摘要：

  雌激素受体（ER）和孕激素受体（PR）在约50％的乳腺癌病变中过表达，并用作生物标记物以对患者进行内分泌治疗。目前，免疫组化（IHC）评估...

  DOI：

  10.1039/c6ra07404a

文献信息

• Cyanopyrrole-containing cyclic carbamate and thiocarbamate biaryls and methods for preparing the same
  申请人：Wilk Kazimierz Bogdan

  公开号：US20050239779A1

  公开（公告）日：2005-10-27

  Methods for preparing cyclic carbamates and thiocarbamates containing cyanopyrrole moieties and of the formula are provided. Z are the same or different and are H, optionally substituted C 1 to C 6 alkyl, or COR A ; R A is H, optionally substituted C 1 to C 6 alkyl, optionally substituted C 1 to C 6 alkoxy, or optionally substituted C 1 to C 6 aminoalkyl; Q are the same or different and are H, OH, NH 2 , CN, halogen, optionally substituted C 1 to C 6 alkyl, optionally substituted C 2 to C 6 alkenyl, optionally substituted C 1 to C 6 alkynyl, optionally substituted C 1 to C 6 alkoxy, optionally substituted C 1 to C 6 aminoalkyl, or COR B ; and R B is H, optionally substituted C 1 to C 6 alkyl, optionally substituted C 1 to C 6 alkoxy, or optionally substituted C 1 to C 6 aminoalkyl. Compounds including 2-amino-5-(5-cyano-1-methyl-1H-pyrrol-2-yl) benzoic acid methyl ester, 5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile, and 2-amino-5-(5-cyano-1-methyl-1H-pyrrol-2-yl)-phenyl-ethanone, or pharmaceutically acceptable salts thereof, and the uses thereof are also provided.

  提供了制备含有氰基吡咯基团的环状碳酸酯和硫代碳酸酯的方法，其化学式如下：Z相同或不同，可以是氢、可选取代的C1到C6烷基或COR A；RA可以是氢、可选取代的C1到C6烷基、可选取代的C1到C6烷氧基或可选取代的C1到C6氨基烷基；Q相同或不同，可以是氢、羟基、氨基、氰基、卤素、可选取代的C1到C6烷基、可选取代的C2到C6烯基、可选取代的C1到C6炔基、可选取代的C1到C6烷氧基、可选取代的C1到C6氨基烷基或COR B；RB可以是氢、可选取代的C1到C6烷基、可选取代的C1到C6烷氧基或可选取代的C1到C6氨基烷基。还提供了包括2-氨基-5-(5-氰基-1-甲基-1H-吡咯-2-基)苯甲酸甲酯、5-[4-氨基-3-(1-羟基-1-甲基-乙基)-苯基]-1-甲基-1H-吡咯-2-碳氰、以及2-氨基-5-(5-氰基-1-甲基-1H-吡咯-2-基)-苯乙酮或其药学上可接受的盐，以及其用途。
• Carbon-11 Radiolabelling of Organosulfur Compounds:¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget
  作者：Tom Haywood、Steven Kealey、Santiago Sánchez-Cabezas、James J. Hall、Louis Allott、Graham Smith、Christophe Plisson、Philip W. Miller

  DOI：10.1002/chem.201501089

  日期：2015.6.15

  Herein a new 11C radiolabelling strategy for the fast and efficient synthesis of thioureas and related derivatives using the novel synthon, 11CS2, is reported. This approach has enabled the facile labelling of a potent progesterone receptor (PR) agonist, [11C]Tanaproget, by the intramolecular reaction of the acyclic aminohydroxyl precursor with 11CS2, which has potential applications as a positron

  本文报道了使用新型合成子11 CS 2快速高效合成硫脲和相关衍生物的新11 C放射性标记策略。该方法通过无环氨基羟基前体与11 CS 2的分子内反应，能够轻松标记强效的孕酮受体（PR）激动剂[ 11 C] Tanaproget ，它有可能作为正电子发射断层扫描放射配体用于癌症成像。
• CYANOPYRROLE CONTAINING CYCLIC CARBAMATE AND THIOCARBAMATE BIARYLS AND METHODS FOR PREPARING THE SAME
  申请人：Wilk Bogdan Kazimierz

  公开号：US20090306371A1

  公开（公告）日：2009-12-10

  Methods for preparing cyclic carbamates and thiocarbamates containing cyanopyrrole moieties and of the formula are provided. Z are the same or different and are H, optionally substituted C 1 to C 6 alkyl, or COR A ; R A is H, optionally substituted C 1 to C 6 alkyl, optionally substituted C 1 to C 6 alkoxy, or optionally substituted C 1 to C 6 aminoalkyl; Q are the same or different and are H, OH, NH 2 , CN, halogen, optionally substituted C 1 to C 6 alkyl, optionally substituted C 2 to C 6 alkenyl, optionally substituted C 1 to C 6 alkynyl, optionally substituted C 1 to C 6 alkoxy, optionally substituted C 1 to C 6 aminoalkyl, or COR B ; and R B is H, optionally substituted C 1 to C 6 alkyl, optionally substituted C 1 to C 6 alkoxy, or optionally substituted C 1 to C 6 aminoalkyl. Compounds including 2-amino-5-(5-cyano-1-methyl-1H-pyrrol-2-yl)benzoic acid methyl ester, 5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile, and 2-amino-5-(5-cyano-1-methyl-1H-pyrrol-2-yl)-phenyl-ethanone, or pharmaceutically acceptable salts thereof, and the uses thereof are also provided.

  提供了制备含有氰基吡咯基团的环状碳酸酯和硫代碳酸酯的方法，其化学式为Z相同或不同，可以是氢，可选取代的C1到C6烷基或CORA；RA为氢，可选取代的C1到C6烷基，可选取代的C1到C6甲氧基，或可选取代的C1到C6氨基烷基；Q相同或不同，可以是氢，羟基，氨基，氰基，卤素，可选取代的C1到C6烷基，可选取代的C2到C6烯基，可选取代的C1到C6炔基，可选取代的C1到C6甲氧基，可选取代的C1到C6氨基烷基，或CORB；RB为氢，可选取代的C1到C6烷基，可选取代的C1到C6甲氧基，或可选取代的C1到C6氨基烷基。还提供了包括2-氨基-5-(5-氰基-1-甲基-1H-吡咯-2-基)苯甲酸甲酯，5-[4-氨基-3-(1-羟基-1-甲基-乙基)-苯基]-1-甲基-1H-吡咯-2-碳腈和2-氨基-5-(5-氰基-1-甲基-1H-吡咯-2-基)-苯乙酮，或其药学上可接受的盐，并提供了它们的用途。
• Cyanopyrrole containing cyclic carbamate and thiocarbamate biaryls and methods for preparing the same
  申请人：Wyeth LLC

  公开号：US08003784B2

  公开（公告）日：2011-08-23

  Methods for preparing cyclic carbamates and thiocarbamates containing cyanopyrrole moieties and of the formula are provided. Z are the same or different and are H, optionally substituted C1 to C6 alkyl, or CORA; RA is H, optionally substituted C1 to C6 alkyl, optionally substituted C1 to C6 alkoxy, or optionally substituted C1 to C6 aminoalkyl; Q are the same or different and are H, OH, NH2, CN, halogen, optionally substituted C1 to C6 alkyl, optionally substituted C2 to C6 alkenyl, optionally substituted C1 to C6 alkynyl, optionally substituted C1 to C6 alkoxy, optionally substituted C1 to C6 aminoalkyl, or CORB; and RB is H, optionally substituted C1 to C6 alkyl, optionally substituted C1 to C6 alkoxy, or optionally substituted C1 to C6 aminoalkyl. Compounds including 2-amino-5-(5-cyano-1-methyl-1H-pyrrol-2-yl)benzoic acid methyl ester, 5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile, and 2-amino-5-(5-cyano-1-methyl-1H-pyrrol-2-yl)-phenyl-ethanone, or pharmaceutically acceptable salts thereof, and the uses thereof are also provided.

  本发明提供了制备含有氰基吡咯基团的环状氨基甲酸酯和硫代氨基甲酸酯的方法，其化学式为Z相同或不同，可以是H，可选取代C1到C6烷基，或者是CORA；RA为H，可选取代C1到C6烷基，可选取代C1到C6烷氧基，或可选取代C1到C6氨基烷基；Q相同或不同，可以是H，OH，NH2，CN，卤素，可选取代C1到C6烷基，可选取代C2到C6烯基，可选取代C1到C6炔基，可选取代C1到C6烷氧基，可选取代C1到C6氨基烷基，或者是CORB；RB为H，可选取代C1到C6烷基，可选取代C1到C6烷氧基，或可选取代C1到C6氨基烷基。本发明还提供了包括2-氨基-5-(5-氰基-1-甲基-1H-吡咯-2-基)苯甲酸甲酯、5-[4-氨基-3-(1-羟基-1-甲基-乙基)-苯基]-1-甲基-1H-吡咯-2-碳腈和2-氨基-5-(5-氰基-1-甲基-1H-吡咯-2-基)-苯乙酮或其药学上可接受的盐，以及它们的用途。
• [EN] CYANOPYRROLE CONTAINING CYCLIC CARBAMATE AND THIOCARBAMATE BIARYLS AND METHODS FOR PREPARING THE SAME<br/>[FR] BIARYLES DE CARBAMATE ET THIOCARBAMATE CYCLIQUES CONTENANT DU CYANOPYRROLE, ET LEURS PROCEDES DE PREPARATION
  申请人：WYETH CORP

  公开号：WO2005105739A3

  公开（公告）日：2006-02-16