3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)propionitrile | 86563-29-3

• 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: 3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)propionitrile
• 英文别名: [(2R,3R,4R,5R,6R)-3,4,5-triacetyloxy-6-(2-cyanoethyl)oxan-2-yl]methyl acetate
• CAS: 86563-29-3
• 化学式: C₁₇H₂₃NO₉
• 分子量: 385.371
• InChiKey: NOXLEHNRIYFCQH-WRQOLXDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)propionitrile 在 二硫代磷酸二乙酯 、 硫代乙酸 作用下， 以49%的产率得到3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thiopropanamide
  参考文献：
  名称：

  Second generation of thiazolylmannosides, FimH antagonists for E. coli-induced Crohn's disease

  摘要：

  E. coli抗粘附剂的化学稳定性通过用短连接剂替代异构氮得到改善。

  DOI：

  10.1039/c6ob00424e
• 作为产物：
  描述：

  丙烯腈 、 alkaline earth salt of/the/ methylsulfuric acid 以 苯 为溶剂， 反应 24.0h， 以75%的产率得到3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)propionitrile
  参考文献：
  名称：

  Ghosez, Anne; Goebel, Thomas; Giese, Bernd, Chemische Berichte, 1988, vol. 121, p. 1807 - 1812

  摘要：

  DOI：

文献信息

• [EN] MANNOSE DERIVATIVES USEFUL FOR TREATING PATHOLOGIES ASSOCIATED WITH ADHERENT E. COLI<br/>[FR] DÉRIVÉS DE MANNOSE UTILES POUR LE TRAITEMENT DE PATHOLOGIES ASSOCIÉES À E. COLI ADHÉRENTS
  申请人：ENTEROME

  公开号：WO2017021549A1

  公开（公告）日：2017-02-09

  The present invention relates to mannose derivatives of formula (I): wherein R1 represents H, CO-(C1-C6)-alkyl or CO-alkylaryl, Y represents a single bond, CH2, O, NR3, S, A represents O, NH or S, X represents H and X' represents OH or X and X' taken together with the carbon atom bearing them form a CO group, R2 represents H, a linear or branched (C1-C6 )-alkyl or CF3, R3 represents H, a C1-C6 alkyl, a CO-(C1-C6 )-alkyl, CF3 or COCF3, and R is as described in claim 1. The mannose derivatives of formulae (I) are useful for treating pathologies associated with the presence of adherent Escherichia coli (AEC), in particular inflammatory bowel diseases (IBD), such as Crohn's disease and ulcerative colitis; a urinary tract infection, in particular painful bladder syndrome and cystitis, more particularly interstitial cystitis; irritable bowel syndrome; metabolic diseases such as metabolic obesity, diabetes, hypercholesterolemia; autoimmune inflammatory diseases; and colorectal cancer, in particular colon cancer.

  本发明涉及式(I)的甘露糖衍生物：其中R1代表H、CO-(C1-C6)-烷基或CO-烷基芳基，Y代表单键、CH2、O、NR3、S，A代表O、NH或S，X代表H，X'代表OH或X和X'与它们相连的碳原子形成CO基团，R2代表H、线性或支链(C1-C6)-烷基或CF3，R3代表H、C1-C6烷基、CO-(C1-C6)-烷基、 或CO ，R如权利要求1中所述。式(I)的甘露糖衍生物对治疗与粘附性大肠埃希菌（AEC）存在相关的病理病变有用，特别是炎症性肠病（IBD），如克罗恩病和溃疡性结肠炎；尿路感染，特别是疼痛性膀胱综合征和膀胱炎，更特别是间质性膀胱炎；肠易激综合征；代谢性疾病，如代谢性肥胖、糖尿病、高胆固醇血症；自身免疫性炎症性疾病；以及结直肠癌，特别是结肠癌。
• Dimeric Metal Complexes as Mediators for Radical C?C Bond-Forming Reactions
  作者：Bernd Giese、Gebhard Thoma

  DOI：10.1002/hlca.19910740523

  日期：1991.8.7

  (2) in the presence of alkyl halides leads to C-centered radicals which can be trappedby alkenes and yields saturated and/or unsaturated addition products. Carbon radicals are generated via halogen abstraction by the initially formed metal-centered radicals resulting from homolysis of the metal-metal bond of dimeric mediators 1 and 2. No reaction occurs using octacarbonyldicobalt (3).

  二羰基的照射（η 5 -环戊二烯基）铁二聚物1或decacarbonyldimanganese（2在烷基卤化物引线的存在对C-中心自由基可以是饱和trappedby烯烃和产率和/或不饱和的加成产物）。碳自由基是由二聚介体1和2的金属-金属键均化而通过最初形成的以金属为中心的自由基通过卤素提取而产生的。使用八羰基二钴（3）不会发生反应。
• Mannose derivatives useful for treating pathologies associated with adherent E. coli
  申请人：ENTEROME

  公开号：US10543223B2

  公开（公告）日：2020-01-28

  The present invention relates to mannose derivatives of formula (I): wherein R1 represents H, CO—(C1-C6)-alkyl or CO-alkylaryl, Y represents a single bond, CH2, O, NR3, S, A represents O, NH or S, X represents H and X′ represents OH or X and X′ taken together with the carbon atom bearing them form a CO group, R2 represents H, a linear or branched (C1-C6)-alkyl or CF3, R3 represents H, a C1-C6 alkyl, a CO—(C1-C6)-alkyl, CF3 or COCF3, and R is as described in claim 1. The mannose derivatives of formulae (I) are useful for treating pathologies associated with the presence of adherent Escherichia coli (AEC), in particular inflammatory bowel diseases (IBD), such as Crohn's disease and ulcerative colitis; a urinary tract infection, in particular painful bladder syndrome and cystitis, more particularly interstitial cystitis; irritable bowel syndrome; metabolic diseases such as metabolic obesity, diabetes, hypercholesterolemia; autoimmune inflammatory diseases; and colorectal cancer, in particular colon cancer.

  本发明涉及式 (I) 的甘露糖衍生物： 其中 R1 代表 H、CO-(C1-C6)-烷基或 CO-烷基芳基、 Y 代表单键、CH2、O、NR3、S、 A 代表 O、NH 或 S、 X 代表 H 和 X′ 代表 OH 或 X 和 X′ 与含有它们的碳原子一起构成 CO 基团、 R2 代表 H、直链或支链（C1-C6）-烷基或 CF3、 R3 代表 H、C1-C6 烷基、CO-(C1-C6)-烷基、 或 CO ，以及 R 如权利要求 1 所述。 式（I）的甘露糖衍生物可用于治疗与粘附性大肠杆菌（AEC）的存在有关的病症，特别是炎症性肠病（IBD），如克罗恩病和溃疡性结肠炎；泌尿道感染，特别是膀胱疼痛综合征和膀胱炎，尤其是间质性膀胱炎；肠易激综合征；代谢性疾病，如代谢性肥胖、糖尿病、高胆固醇血症；自身免疫性炎症；以及结肠直肠癌，特别是结肠癌。
• Giese, Bernd; Dupuis, Jacques, Angewandte Chemie, 1983, vol. 95, # 8, p. 633 - 634
  作者：Giese, Bernd、Dupuis, Jacques

  DOI：——

  日期：——
• Readman; Marsden; Hodgson, Synlett, 2000, # 11, p. 1628 - 1630
  作者：Readman、Marsden、Hodgson

  DOI：——

  日期：——