5-(3,3,6-trimethyl-indan-5-yloxy)furan-2-carboxylic acid | 478010-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(3,3,6-trimethyl-indan-5-yloxy)furan-2-carboxylic acid
• 英文别名: 5-[(3,3,6-Trimethyl-1,2-dihydroinden-5-yl)oxy]furan-2-carboxylic acid
• CAS: 478010-72-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: FPUIDTGMOZUWMV-UHFFFAOYSA-N

物化性质

• 沸点：
  403.1±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3,3,6-trimethyl-indan-5-yloxy)furan-2-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-chloro-4,6-dimethoxypyrimidin-5-yl)-5-((3,3,6-trimethyl-2,3-dihydro-1H-inden-5-yl)oxy)furan-2-carboxamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of small-molecule [18F] labeled gonadotropin-releasing hormone (GnRH) receptor antagonists as potential PET imaging agents for GnRH receptor expression

  摘要：

  Two novel small molecule gonadotropin-releasing hormone (GnRH) receptor antagonists (12 and 13) of the furamide-class were synthesized and evaluated in vitro for their receptor binding affinities for the rat GnRH receptor. Radiolabeling with no carrier added fluorine-18 of the appropriate precursors was investigated in a one-step reaction. LogP (Octanol/PBS pH 7.4) and serum stability of the compounds were investigated. The antagonists showed low nM affinity for the rat GnRH receptor. F-18-radiolabled compounds were obtained in high radiochemical purity (> 95%) and specific activity (> 75 GBq/mu mol). These findings suggest this class of compounds holds promise as potential probes for PET targeting of GnRHreceptor expression. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.002
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 palladium on activated charcoal sodium hydroxide 、 PPA 、 硫酸 、 氢气 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~105.0 ℃ 、275.79 kPa 条件下， 反应 7.0h， 生成 5-(3,3,6-trimethyl-indan-5-yloxy)furan-2-carboxylic acid
  参考文献：
  名称：

  发现了一种新型的口服活性小分子促性腺激素释放激素（GnRH）受体拮抗剂。

  摘要：

  促性腺激素释放激素（GnRH）在生殖生物学中起重要作用。在文献中已经报道了使用GnRH受体拮抗剂来治疗乳腺癌，卵巢癌和前列腺癌。在本文中，我们报告了口服生物利用的有效小分子GnRH受体拮抗剂N- {4,6-二甲氧基-2-[（3-吗啉-4-基丙基）]的合成，体外表征，药代动力学和药效学氨基]嘧啶-5-基} -5- [3,3,6-三基-2,3-二氢-1H-茚基-5-基）氧基] -2-呋喃酰胺（化合物1）。

  DOI：

  10.1021/jm060012g

文献信息

• [EN] RADIOLABELED GNRH ANTAGONISTS AS PET IMAGING AGENTS<br/>[FR] ANTAGONISTES DE LA GONADOTROPHINE (GNRH) RADIOMARQUÉS UTILISÉS COMME AGENTS D'IMAGERIE PAR TOMOGRAPHIE PAR ÉMISSION DE POSITRONS (TEP)
  申请人：UNIV OSLO HF

  公开号：WO2014184682A9

  公开（公告）日：2015-01-29
• NON-PEPTIDE GNRH AGENTS, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR THEIR USES, AND PROCESSES FOR PREPARING THEM
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：EP1401427A2

  公开（公告）日：2004-03-31
• EP1401427A4
  申请人：——

  公开号：EP1401427A4

  公开（公告）日：2004-12-01
• RADIOLABELED GNRH ANTAGONISTS AS PET IMAGING AGENTS
  申请人：OSLO UNIVERSITETSSYKEHUS HF

  公开号：US20160058895A1

  公开（公告）日：2016-03-03

  Provided herein is technology relating to imaging agents for positron emission tomography (PET) and particularly, but not exclusively, to a gonadotropin-releasing hormone (GnRH) antagonist radiolabeled with positron emitting nuclides and to methods of visualizing GnRH receptors in the central nervous system by PET from administration of such compounds to warm-blooded animals for diagnostic purposes.
• [EN] NON-PEPTIDE GNRH AGENTS, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR THEIR USE, AND PROCESSES FOR PREPARING THEM AND THEIR INTERMEDIATES<br/>[FR] AGENTS GNRH NON PEPTIDIQUES, COMPOSITIONS PHARMACEUTIQUES ET METHODES D'UTILISATION DE CES DERNIERES, PROCEDES DE PREPARATION DE CES COMPOSES ET DE LEURS INTERMEDIAIRES
  申请人：AGOURON PHARMA

  公开号：WO2002098363A2

  公开（公告）日：2002-12-12

  Non-peptide GnRH agents capable of inhibiting the effect of gonadotropin-releasing hormone are described. Such compounds and their pharmaceutically acceptable salts, prodrugs, and active metabolites are suitable for treating mammalian reproductive disorders and steroid hormone-dependent tumors as well as for regulating fertility, where suppression of gonadotropin release is indicated. Methods for synthesizing the compounds and intermediates useful in their preparation are also described.