2-脱氧-2-氨基-b-D-葡萄糖 | 14257-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧-2-氨基-b-D-葡萄糖
• 英文名称: glucosamine
• 英文别名: D-glucosamine；2-amino-2-deoxy-D-glucose；GlcN；2-Amino-2-deoxy-β-D-glucopyranose；beta-D-Glucosamine；(2R,3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
• CAS: 14257-69-3
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: MSWZFWKMSRAUBD-QZABAPFNSA-N

物化性质

• 熔点：
  110 °C (decomp)
• 沸点：
  449.9±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)
• 碰撞截面：
  134.7 Ų [M+H]+; 146.3 Ų [M+Na]+

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  6

ADMET

毒理性

• 在妊娠和哺乳期间的影响

哺乳期使用概述：氨基葡萄糖是一种氨基单糖，可以从贝类中提取或合成生产。氨基葡萄糖硫酸盐没有特定的与哺乳相关的用途。它最常用于治疗骨关节炎。氨基葡萄糖的衍生物，N-乙酰氨基葡萄糖，是人类母乳的正常成分。氨基葡萄糖硫酸盐耐受性良好，偶尔会有胃肠道不适（如腹泻、胃灼热、恶心、呕吐）的报告。尽管没有关于哺乳期间使用氨基葡萄糖硫酸盐的研究，但哺乳母亲使用它不太可能对哺乳婴儿产生不利影响。 膳食补充剂不需要美国食品药品监督管理局的广泛市场前批准。制造商负责确保产品的安全性，但在上市前不需要证明膳食补充剂的安全性和有效性。膳食补充剂可能含有多种成分，标签上标注的成分或其含量与实际成分或含量之间常常存在差异。制造商可以与独立组织签订合同，以验证产品的质量或其成分，但这并不证明产品的安全或有效性。由于上述问题，一个产品的临床测试结果可能不适用于其他产品。有关膳食补充剂的更详细信息可以在LactMed网站的其它地方找到。 对哺乳婴儿的影响：截至修订日期，没有找到相关的已发布信息。 对泌乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:Glucosamine is an amino-monosaccharide that is either derived from shellfish or synthetically produced. Glucosamine sulfate has no specific lactation-related uses. It is most commonly used to treat osteoarthritis. A glucosamine derivative, N-acetylglucosamine, is a normal component of human breastmilk. Glucosamine sulfate is well tolerated with occasional gastrointestinal discomfort (e.g., diarrhea, heartburn, nausea, vomiting) reported. Although no studies exist on the use of glucosamine sulfate during breastfeeding, its use by a nursing mother is unlikely to adversely affect the breastfed infant. Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

反应信息

• 作为反应物：
  描述：

  2-脱氧-2-氨基-b-D-葡萄糖 在 吡啶 、 三乙胺 作用下， 反应 16.0h， 生成 2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖
  参考文献：
  名称：

  Grover, Parul; Singh, Jitender; Dhar, Journal of the Indian Chemical Society, 2009, vol. 86, # 10, p. 1112 - 1114

  摘要：

  DOI：
• 作为产物：
  描述：

  chitosan 在 盐酸 、 水 作用下， 反应 3.0h， 生成 2-脱氧-2-氨基-b-D-葡萄糖
  参考文献：
  名称：

  Suppression of cytokine production in lipopolysaccharide-stimulated mouse macrophages by novel cationic glucosamine derivative involves down-regulation of NF-κB and MAPK expressions

  摘要：

  Exposure of macrophages to bacterial lipopolysaccharide (LPS) induces release of proinflammatory cytokines that play crucial roles in chronic inflammation. Glucosamine has reported to possess anti-inflammatory properties and currently is the oral supplement of choice for the management of inflammation related complications including osteoarthritis. In this study, quaternized amino glucosamine (QAGlc), a newly synthesized cationic glucosamine (Glc) derivative was found to inhibit LPS-stimulated production of IL-1 beta, IL-6, TNF-alpha, and PGE(2) in RAW264.7, mouse macrophages more potently than its starting material Glc. Since production of cytokines is regulated mainly via activation of NF-kappa B and regulation of mitogen-activated protein kinases (MAPKs), we examined if QAGlc could be responsible for the suppression of NF-kappa B pathway and MAPKs. We used reporter gene assay and Western blotting to examine the effects of QAGlc on activation and translocation of NF-kappa B. Further, QAGlc-mediated inhibition of NF-kappa B was accompanied with a suppression of its translocation. Apparently, QAGlc was shown to attenuate LPS-induced activation of p38 MAPK and JNK in RAW264.7 cells suggesting that inhibition of MAPK-mediated LPS signaling also contribute to suppression of cytokine production following stimulation of macrophages with LPS. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.037
• 作为试剂：
  描述：

  2-溴吡啶 、 苯乙烯 在 2-脱氧-2-氨基-b-D-葡萄糖 、 palladium diacetate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以62%的产率得到3-苯乙烯基吡啶
  参考文献：
  名称：

  d-氨基葡萄糖作为钯催化芳基和杂芳基卤化物交叉偶联的绿色配体

  摘要：

  在钯催化的芳基和杂芳基卤化物的 Heck 偶联中，天然存在的 d-葡糖胺可作为膦的有效绿色替代品。一系列反式二苯乙烯衍生物、芳基萘基烯烃、杂芳基烯烃和 β-芳基取代的丙烯酸酯已在较短的反应时间内以中等至高产率合成。

  DOI：

  10.1055/s-0034-1379612

文献信息

• [EN] IMIDAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS IMIDAZOLE UTILES COMME INHIBITEURS DE LA FAAH
  申请人：MERCK & CO INC

  公开号：WO2009152025A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzeimer Disease, and Parkinson's Disease.

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病性神经病、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• [EN] PYRAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2009151991A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzheimer disease, and Parkinson's disease

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• [EN] BICYCLIC ARYL SPHINGOSINE 1-PHOSPHATE ANALOGS<br/>[FR] ANALOGUES D’ARYLSPHINGOSINE-1-PHOSPHATE BICYCLIQUES
  申请人：BIOGEN IDEC INC

  公开号：WO2011017561A1

  公开（公告）日：2011-02-10

  Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.

  提供具有在一个或多个SlP受体上拮抗活性的化合物。这些化合物是鞘氨醇类似物，在磷酸化后可以在SlP受体上表现为拮抗剂。
• [EN] OXAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS D'OXAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2010017079A1

  公开（公告）日：2010-02-11

  The present invention is directed to certain oxazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzeimer Disease, and Parkinson's Disease.

  本发明涉及某些噁唑衍生物，其可用作脂肪酸酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• [EN] THIENOPYRIDONE DERIVATIVES AS AMP-ACTIVATED PROTEIN KINASE (AMPK) ACTIVATORS<br/>[FR] DÉRIVÉS DE THÉNOPYRIDONE COMME ACTIVATEURS DE LA PROTÉINE KINASE DÉPENDANTE DE L'AMP (AMPK)
  申请人：MERCK PATENT GMBH

  公开号：WO2009124636A1

  公开（公告）日：2009-10-15

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in claim 1, including pharmaceutical compositions thereof and for their use in the treatment and/or prevention of diseases and disorders modulated by AMP agonists. The invention is also directed to intermediates and to a method of preparation of compounds of formula (I).

  本发明涉及式(I)的化合物，其中R1、R2和R3如权利要求1所定义，包括其药物组合物以及用于治疗和/或预防由AMP激动剂调节的疾病和紊乱的用途。该发明还涉及中间体和式(I)化合物的制备方法。

表征谱图