4H-噻吩并[3,2-c]苯并吡喃-2-羧酸 | 26268-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 4H-噻吩并[3,2-c]苯并吡喃-2-羧酸
• 英文名称: 4H-thieno[3,2-c]-chromene-2-carboxylic acid
• 英文别名: 4H-thieno[3,2-c]chromene-2-carboxylic acid
• CAS: 26268-04-2
• 化学式: C₁₂H₈O₃S
• mdl: MFCD06335025
• 分子量: 232.26
• InChiKey: ZMEWPWRPNHFDRC-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4H-噻吩并[3,2-c]苯并吡喃-2-羧酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 2-azidoethyl (5-acetamido-9-(4H-thieno[3,2-c]chromene-2-carboxamido)-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  In Silico-Aided Design of a Glycan Ligand of Sialoadhesin for in Vivo Targeting of Macrophages

  摘要：

  Cell-specific delivery of therapeutic agents using ligand targeting is gaining interest because of its potential for increased efficacy and reduced side effects. The challenge is to develop a suitable ligand for a cell-surface receptor that is selectively expressed on the desired cell. Sialoadhesin (Sn, Siglec-1, CD169), a sialic acid-binding immunoglobulin-like lectin (Siglec) expressed on subsets of resident and inflammatory macrophages, is an attractive target for the development of a ligand-targeted delivery system. Here we report the development of a high-affinity and selective ligancl for Sn that is an analogue of the natural ligand and is capable of targeting liposomal nanoparticles to Sn-expressing cells in vivo. An efficient in silico screen of a library of similar to 8400 carboxylic acids was the key to identifying novel 9-N-acyl-substituted N-acetylneuramic acid (Neu5Ac) substituents as potential lead compounds. A small panel of targets were selected from the screen and synthesized to evaluate their affinities and selectivities. The most potent of these Sn ligands, (4H-thieno[3,2-c]chromene-2-carbamoyl)-Neu5Ac alpha 2-3Gal beta 1-4GlcNAc ((TCC)Neu5Ac), was conjugated to lipids for display on a liposomal nanoparticle for evaluation of targeted delivery to cells. The (TCC)Neu5Ac liposomes were found to target liposomes selectively to cells expressing either murine or human Sn in vitro, and when administered to mice, they exhibited in vivo targeting to Sn-positive macrophages.

  DOI：

  10.1021/ja307501e
• 作为产物：
  描述：

  2-(ethoxycarbonyl)-4H-thieno<3,2-c><1>benzopyran 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4H-噻吩并[3,2-c]苯并吡喃-2-羧酸
  参考文献：
  名称：

  4H-Thieno[3,2-c]chromene based inhibitors of Notum Pectinacetylesterase

  摘要：

  A group of small molecule thienochromenes inhibitors of Notum Pectinacetylesterase are described. We developed SAR on three series based on carbon, oxygen and sulfur replacement of the 5-position. In each series, highly potent Notum Pectinacetylesterase inhibitors were identified. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.038

文献信息

• BENZOPYRAN AND BENZOXEPIN PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
  申请人：Do Steven

  公开号：US20090247567A1

  公开（公告）日：2009-10-01

  Benzopyran and benzoxepin compounds of Formulas I and II, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formulas I and II for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  Benzopyran和benzoxePIn的化合物I和II的分子式，包括其立体异构体、几何异构体、互变异构体、溶剂合物、代谢物和药学上可接受的盐，可用于抑制脂质激酶，包括p110 alpha和PI3K的其他同系物，并用于治疗由脂质激酶介导的癌症等疾病。公开了使用分子式I和II的化合物在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗此类疾病或相关病理条件的方法。
• 4H-THIENO[3,2-C]CHROMENE-BASED INHIBITORS OF NOTUM PECTINACETYLESTERASE AND METHODS OF THEIR USE
  申请人：BARBOSA Joseph

  公开号：US20120302562A1

  公开（公告）日：2012-11-29

  Compounds that may be used to inhibit Notum Pectinacetylesterase are described, as well as compositions comprising them, and methods of their use to treat diseases and disorders affecting bone.

  描述了可以用来抑制Notum果胶乙酰酯酶的化合物，以及包含它们的组合物，以及它们用于治疗影响骨骼的疾病和紊乱的方法。
• 一种基于氨基唾液酸糖的CD169亲和荧光探 针TCC-FITC及其制备方法
  申请人：厦门诺康得生物科技有限公司

  公开号：CN108299472B

  公开（公告）日：2019-08-27

  本发明公开了一种基于氨基唾液酸糖的CD169亲和荧光探针TCC‑FITC及其制备方法，其结构式如下：本发明的基于氨基唾液酸糖的CD169亲和荧光探针TCC‑FITC针对CD169靶点具有高亲和力，能够良好的在体内和体外定位含有CD169+巨噬细胞的肿瘤组织。
• [EN] PYRAZINE AND IMIDAZOLIDINE DERIVATIVES AND THEIR USES TO TREAT HEPATITIS C<br/>[FR] DÉRIVÉS DE PYRAZINE ET D'IMIDAZOLIDINE ET LEURS UTILISATIONS EN VUE DU TRAITEMENT DE L'HÉPATITE C
  申请人：GILEAD PHARMASSET LLC

  公开号：WO2012103113A1

  公开（公告）日：2012-08-02

  Disclosed herein are compounds useful for treating a viral infection, such HCV.

  本文披露了一些用于治疗病毒感染，如HCV的化合物。
• 一种CD169高亲和力抗肿瘤化合物及其制备 方法和应用
  申请人：厦门诺康得生物科技有限公司

  公开号：CN107501291B

  公开（公告）日：2020-01-21

  本发明提供的一种CD169高亲和力抗肿瘤化合物及其制备方法和应用，CD169高亲和力抗肿瘤化合物为一种小分子抗肿瘤化合物，可以利用其特异的、广谱的性质对肿瘤进行杀伤。TCC‑Neu5Ac靶向体内的肿瘤，经过代谢生长在肿瘤细胞的表面，形成TCC‑Neu5Ac配体。肿瘤附近的巨噬细胞识别后，将其吞噬，同时释放出肿瘤碎片并呈递给其它免疫细胞，引发抗肿瘤免疫反应。本发明提供的CD169高亲和力抗肿瘤化合物对多种肿瘤均有效，对肿瘤转移也有抑制效果。此外，本发明提供的CD169高亲和力抗肿瘤化合物不仅可以注射，还可以通过口服发挥作用，其细胞毒性和动物毒性均很低，具有广阔应用前景和市场价值。