4-bromomethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole | 70380-26-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-bromomethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole
• 英文别名: tetra-O-acetyl-1-(4-bromomethyl-[1,2,3]triazol-1-yl)-β-D-1-deoxy-glucopyranose；4-(bromomethyl)-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2,3-triazole；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-(bromomethyl)triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 70380-26-6
• 化学式: C₁₇H₂₂BrN₃O₉
• 分子量: 492.28
• InChiKey: WRLXKHDYECUQBV-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-bromomethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole 在 甲醇 、 sodium methylate 作用下， 以 乙酸乙酯 为溶剂， 反应 17.0h， 生成 diethyl {[1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl]methyl}phosphonate
  参考文献：
  名称：

  Synthesis of 4-amidomethyl-1-glucosyl-1,2,3-triazoles and evaluation as glycogen phosphorylase inhibitors

  摘要：

  Glycogen phosphorylase (GP) appears as a key enzyme for the control of hyperglycemia in the context of type 2 diabetes. In order to gain additional data for structure-activity studies of the inhibition of this enzyme, a series of eight GP inhibitor candidates were prepared from peracetylglucopyranosyl azide 1 by click-chemistry. The need for a N-Boc-protected propargylamine was identified in the CuAAC with azide 1 under Meldal's conditions, while Sharpless' conditions were better adapted to the CuAAC of azide 1 with propargyl bromide. Cycloaddition of Boc-propargylamine with azide 1 afforded the N-Boc precursor of a 4-aminomethyl-1-glucosyl-1,2,3-triazole which gave access to a series of eight amide and sulfonamide derivatives. After deacetylation, enzymatic studies revealed poor to moderate inhibitions toward this enzyme. The N-Boc-protected amine was the best inhibitor (IC50 = 620 mu M) unexpectedly slightly better than the 2-naphthylamido substituted analogue (IC50 = 650 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.10.009
• 作为产物：
  描述：

  3-溴丙炔 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以85%的产率得到4-bromomethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of 4-amidomethyl-1-glucosyl-1,2,3-triazoles and evaluation as glycogen phosphorylase inhibitors

  摘要：

  Glycogen phosphorylase (GP) appears as a key enzyme for the control of hyperglycemia in the context of type 2 diabetes. In order to gain additional data for structure-activity studies of the inhibition of this enzyme, a series of eight GP inhibitor candidates were prepared from peracetylglucopyranosyl azide 1 by click-chemistry. The need for a N-Boc-protected propargylamine was identified in the CuAAC with azide 1 under Meldal's conditions, while Sharpless' conditions were better adapted to the CuAAC of azide 1 with propargyl bromide. Cycloaddition of Boc-propargylamine with azide 1 afforded the N-Boc precursor of a 4-aminomethyl-1-glucosyl-1,2,3-triazole which gave access to a series of eight amide and sulfonamide derivatives. After deacetylation, enzymatic studies revealed poor to moderate inhibitions toward this enzyme. The N-Boc-protected amine was the best inhibitor (IC50 = 620 mu M) unexpectedly slightly better than the 2-naphthylamido substituted analogue (IC50 = 650 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.10.009

文献信息

• [EN] NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT TRANSPORTER<br/>[FR] NOUVEAUX COMPOSES POSSEDANT UNE ACTIVITE INHIBITRICE DIRIGEE CONTRE LE TRANSPORTEUR DEPENDANT DU SODIUM
  申请人：TANABE SEIYAKU CO

  公开号：WO2005012326A1

  公开（公告）日：2005-02-10

  A compound of the formula (I) wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is -(CH2)n- (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  化合物的式子（I）其中环A和环B为：（1）环A是可选取代的不饱和单环杂环，环B是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A是可选取代的苯环，环B是可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或（3）环A是可选取代的不饱和融合杂双环，环B独立地是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是碳原子或氮原子；Y是-(CH2)n-（n为1或2）；其药物可接受的盐或前药。
• Novel compounds
  申请人：Nomura Sumihiro

  公开号：US20050233988A1

  公开（公告）日：2005-10-20

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物，其化学式为：其中环A和环B分别为：（1）环A为可选取代的不饱和单环杂环，环B为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；（2）环A为可选取代的苯环，环B为可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环；或（3）环A为可选取代的不饱和融合杂双环，环B独立地为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X为碳原子或氮原子；Y为—（CH2）n—（n为1或2）；其药学上可接受的盐或其前药。
• GLUCOPYRANOSIDE COMPOUND
  申请人：NOMURA Sumihiro

  公开号：US20120258913A1

  公开（公告）日：2012-10-11

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物的公式：其中环A和环B是：(1) 环A是一个可选取代的不饱和单环杂环，环B是一个可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，(2) 环A是一个可选取代的苯环，环B是一个可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或(3) 环A是一个可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是一个碳原子或氮原子；Y是—(CH2)n—(n为1或2)；或其药学上可接受的盐或前药。
• Glucopyranoside compound
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US08202984B2

  公开（公告）日：2012-06-19

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH2)n— (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  该化合物的化学式为：其中环A和环B分别为：（1）环A是可选取代的不饱和单环杂环，环B是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A是可选取代的苯环，环B是可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或（3）环A是可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是碳原子或氮原子；Y是—(CH2)n—（n为1或2）；或其药学上可接受的盐或前药。
• Novel compounds having inhibitory activity against sodium-dependant glucose transporter
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2514756A1

  公开（公告）日：2012-10-24

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is ―(CH2)n-(n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  式中的化合物： 其中环 A 和环 B 是(1) 环 A 是被任选取代的不饱和单环杂环，环 B 是被任选取代的不饱和单环杂环、被任选取代的不饱和融合杂环或被任选取代的苯环环 B 是任选取代的不饱和单环杂环或任选取代的不饱和融合杂环，或 (3) 环 A 是任选取代的不饱和融合杂环，环 B 独立地是任选取代的不饱和单环杂环、任选取代的不饱和融合杂环或任选取代的苯环；X 是碳原子或氮原子； Y 是-(CH2)n-(n 是 1 或 2)； 其药学上可接受的盐，或其原药。