2-deoxy-2-amino glucose | 3416-24-8

• 物质功能分类: 原料药 - 解热镇痛药 - 抗痛风药
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-amino glucose
• 英文别名: D-glucosamine；glucosamine；(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
• CAS: 3416-24-8
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: MSWZFWKMSRAUBD-IVMDWMLBSA-N

物化性质

• 沸点：
  311.69°C (rough estimate)
• 密度：
  1.3767 (rough estimate)
• 溶解度：
  DMSO:23.0(最大浓度 mg/mL);128.37(最大浓度 mM)水:36.0(最大浓度 mg/mL);200.93(最大浓度 mM)
• 熔点：
  88 °C
• LogP：
  -2.175 (est)
• 物理描述：
  Solid
• 蒸汽压力：
  9.02X10-8 mm Hg at 25 °C (est)
• 解离常数：
  pKa = 7.58
• 碰撞截面：
  132.9 Ų [M+H-H2O]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

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

代谢

葡萄糖胺在肝脏中发生代谢。文献中对葡萄糖胺的代谢信息有限。

Glucosamine undergoes metabolism in the liver. Metabolism information for glucosamine is limited in the literature.

来源:DrugBank

毒理性

• 肝毒性

在对照试验中，葡萄糖胺及其与软骨素的组合并未与血清酶升高或临床上明显的肝损伤病例有关联。此外，从前瞻性试验中也没有报告临床上明显的肝损伤病例。近期，有几份病例报告和小的病例系列出版物提到，归因于葡萄糖胺（单独或与软骨素合用）的临床上明显的肝损伤，但是葡萄糖胺本身与其他草药产品中涉及的成分或潜在污染物之间的关系仍然不明确，有几例仅被认为是“可能”与葡萄糖胺相关。发病时间通常在开始服用该制剂后1到4周，损伤模式通常是肝细胞型或混合型。至少有一例急性肝衰竭的报告。免疫过敏特征（皮疹、发热、嗜酸性粒细胞增多）可能出现，但通常不显著。大多数患者在停止服用后4到8周内报告恢复。尚未有葡萄糖胺再挑战的实例，且使用的葡萄糖胺产品的纯度和浓度尚未报告。

In controlled trials, glucosamine and its combination with chondroitin have not been linked to serum enzyme elevations or to instances of clinically apparent liver injury. In addition, cases of clinically apparent liver injury have not been reported from prospective trials. Recently, several cases reports and small series of clinically apprent liver injury attributed to glucosamine (with or without chondroitin) have been published, but the relationship of glucosamine itself as opposed to other herbals in the implicated products or to potential contaminants, remains unclear and several cases were considered only "possibly" related to glucosamine. The time to onset is usually 1 to 4 weeks after starting the preparation and the pattern of injury is typically hepatocellular or mixed. At least one instance of acute liver failure has been reported. Immunoallergic features (rash, fever, eosinophilia) can occur, but are usually not prominent. Most patients were reported to recover within 4 to 8 weeks of stopping. There have not been instances of rechallenge with glucosamine, and the purity and concentration of glucosamine in the products used have not been reported.

来源:LiverTox

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用概述：氨基单糖是一种从甲壳类动物中提取或合成产生的氨基单糖。氨基单糖硫酸盐与哺乳无特定关联，主要用于治疗骨关节炎。氨基单糖衍生物，N-乙酰氨基葡萄糖，是正常的人类母乳成分。氨基单糖硫酸盐耐受性良好，偶尔会出现胃肠道不适（例如，腹泻、胃灼热、恶心、呕吐）的报道。尽管没有关于哺乳期间使用氨基单糖硫酸盐的研究，但哺乳母亲使用该药物对哺乳婴儿不太可能有不利影响。 ◉ 婴儿哺乳期间的效果：截至修订日期，没有找到相关的已发布信息。 ◉ 对哺乳和母乳的影响：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)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。密切观察呼吸不足的迹象，如有需要，进行辅助通气。通过非重复呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时进行治疗……。监测休克，并在必要时进行治疗……。预防癫痫发作，并在必要时进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用带气囊的面罩进行正压通气技术可能有益。考虑使用药物治疗肺水肿...。对于严重的支气管痉挛，可以考虑给予β激动剂，如沙丁胺醇...。监测心率和必要时治疗心律失常...。开始静脉输注5%葡萄糖水（D5W）/SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%盐水（NS）或乳酸林格液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象...。使用地西泮或劳拉西泮治疗癫痫...。使用丙美卡因氢氯化物协助眼部冲洗...。/Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验动物：急性暴露/ 葡萄糖胺（Glmn），通过己糖胺途径的葡萄糖代谢产物，通过阻碍胰岛素诱导的GLUT 4葡萄糖转运蛋白向质膜的转位，导致孤立的脂肪细胞产生胰岛素抵抗。/有/假设Glmn通过类似的机制在骨骼肌中引起胰岛素抵抗。在清醒的雄性Sprague-Dawley大鼠中进行了正常血糖高胰岛素钳夹实验（12 mU/kg/min + 3H-3-葡萄糖），并给予或不给予Glmn输注，输注速率从0.1到6.5 mg/kg/min不等。在4小时的正常血糖钳夹后，后肢肌肉被快速冷冻并匀浆，膜通过差速离心分离并使用不连续的蔗糖梯度（25%，30%和35%蔗糖）分离。膜蛋白被溶解并通过免疫印迹法检测GLUT 4。使用Glmn时，葡萄糖摄取（GU）最大减少了33 +/- 1%，P < 0.001。使GU最大减少50%的Glmn剂量为0.1 mg/kg/min，或者是GU摩尔速率的1/70。对照的半乳糖胺和甘露糖胺输注对GU没有影响。相对于基线，胰岛素使25%膜组分（f）中的GLUT 4增加了2.6倍，P < 0.01，使35%f中的GLUT 4减少了40%，P < 0.05，但对30%f中的GLUT 4没有影响，P= NS。在胰岛素中加入Glmn导致25%f中的GLUT 4减少了41%，P < 0.05，30%f中下降了29%，并阻止了35%f中GLUT 4的减少。将30%f膜用27%和30%蔗糖梯度进行第二次分离。胰岛素使GLUT 4从30%f中移出，P < 0.05，但对27%f没有影响。相比之下，Glmn减少了27%f中的GLUT 4，P < 0.05，但对30%f没有影响。因此，Glmn似乎改变了胰岛素不敏感的GLUT 4池的转位。同时输注Glmn没有改变25、30或35%f中肌膜标记物5'-核苷酸酶、Na+/K+ATP酶和磷脂蛋白的富集。因此，Glmn完全阻断了胰岛素诱导的Glut 4的移动。Glmn是体内胰岛素抵抗的强诱导剂，因为它至少部分引起了GLUT 4转位和/或运输的内在缺陷。这些数据支持Glmn可能导致葡萄糖诱导的胰岛素抵抗（葡萄糖毒性）的潜在作用。

/LABORATORY ANIMALS: Acute Exposure/ Glucosamine (Glmn), a product of glucose metabolism via the hexosamine pathway, causes insulin resistance in isolated adipocytes by impairing insulin-induced GLUT 4 glucose transporter translocation to the plasma membrane. /It was/ hypothesized that Glmn causes insulin resistance in vivo by a similar mechanism in skeletal muscle. Euglycemic hyperinsulinemic clamps (12 mU/kg/min + 3H-3-glucose) /were performed/ in awake male Sprague-Dawley rats with and without Glmn infusion at rates ranging from 0.1 to 6.5 mg/kg/min. After 4h of euglycemic clamping, hindquarter muscles were quick-frozen and homogenized, and membranes were subfractionated by differential centrifugation and separated on a discontinuous sucrose gradient (25, 30, and 35% sucrose). Membrane proteins were solubilized and immunoblotted for GLUT 4. With Glmn, glucose uptake (GU) was maximally reduced by 33 +/- 1%, P < 0.001. The apparent Glmn dose to reduce maximal GU by 50% was 0.1 mg/kg/min or 1/70th the rate of GU on a molar basis. Control galactosamine and mannosamine infusions had no effect on GU. Relative to baseline, insulin caused a 2.6-fold increase in GLUT 4 in the 25% membrane fraction (f), P < 0.01, and a 40% reduction in the 35%f, P < 0.05, but had no effect on GLUT 4 in the 30% f, P= NS. Addition of Glmn to insulin caused a 41% reduction of GLUT 4 in the 25%f, P < 0.05, a 29% fall in the 30%f, and prevented the reduction of GLUT 4 in the 35% f. The 30%f membranes were subjected to a second separation with a 27 and 30% sucrose gradient. Insulin mobilized GLUT 4 away from the 30%f, P < 0.05, but not the 27% f. In contrast, Glmn reduced GLUT 4 in the 27%f, P < 0.05, but not the 30%f. Thus Glmn appears to alter translocation of an insulin-insensitive GLUT 4 pool. Coinfusion of Glmn did not alter enrichment of the sarcolemmal markers 5'-nucleotidase, Na+/K+ATPase, and phospholemman in either 25, 30, or 35% f. Thus Glmn completely blocked movement of Glut 4 induced by insulin. Glmn is a potent inducer of insulin resistance in vivo by causing (at least in part) a defect intrinsic to GLUT 4 translocation and/or trafficking. These data support a potential role for Glmn to cause glucose-induced insulin resistance (glucose toxicity).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

• 吸收

在一项药代动力学研究中，氨基葡萄糖通过胃肠道的吸收率为88.7%。绝对口服生物利用度为44%，这可能是由于肝脏的首过效应。在一项针对12名健康成人的口服结晶氨基葡萄糖的药代动力学研究中，血浆水平可增加至基线水平的30倍，单次1500毫克剂量下的Cmax（最高血药浓度）为10微摩尔。Tmax（达到最高血药浓度的时间）约为3小时。在服用15000毫克剂量后，AUC（血药浓度-时间曲线下面积）为20216 ± 5021。

In a pharmacokinetic study, glucosamine was 88.7% absorption by the gastrointestinal tract. Absolute oral bioavailability was 44%, likely due to the hepatic first-pass effect. In a pharmacokinetic study of 12 healthy adults receiving oral crystalline glucosamine, plasma levels increased up to 30 times the baseline levels and Cmax was 10 microM with a 1,500 mg once-daily dose. Tmax was about 3 hours. AUC was 20,216 ± 5021 after a 15,000 mg dose.

来源:DrugBank

吸收、分配和排泄

• 消除途径

在药物代谢动力学研究中，120小时内葡萄糖胺的粪便排泄率为11.3%。在给药后的前8小时内，尿液排泄率为1.19%。

Fecal excretion of glucosamine in a pharmacokinetic study was 11.3% within 120 hours after administration. Urinary elimination was found to be 1.19% within the first 8 hours post-administration.

来源:DrugBank

吸收、分配和排泄

• 分布容积

一项对12名健康志愿者连续三天每天口服硫酸氨基葡萄糖可溶性粉剂的药代动力学研究结果显示，氨基葡萄糖分布到血管外间隙。文献中关于氨基葡萄糖的人体药代动力学数据有限，然而，在一项大型动物模型研究中，对马的研究揭示了一个平均表观分布体积为15.4 L/kg。静脉给药后，氨基葡萄糖的浓度范围为9-15微摩尔，经鼻胃管给药后为0.3-0.7微摩尔。这些浓度在大多数马给药后12小时内保持在0.1-0.7微摩尔的范围内，这表明一日一次剂量是有效的。在大鼠和狗中，从C-14标记的氨基葡萄糖剂量中检测到的放射性物质存在于肝脏、肾脏、关节软骨和其他区域。

Results of a pharmacokinetic study of 12 healthy volunteers receiving three daily consecutive oral administrations of glucosamine sulfate soluble powder demonstrated glucosamine distribution to extravascular compartments. Human pharmacokinetic data for glucosamine is limited in the literature, however, a large animal model study of horses revealed a mean apparent volume of distribution of 15.4 L/kg. Concentrations of glucosamine ranged from 9-15 microM after an intravenous dose, and 0.3-0.7 microM after nasogastric dosing. These concentrations remained in the range of 0.1-0.7 microM in the majority of horses 12 hours after dosing, suggesting effectiveness of a once-daily dose. In rats and dogs, radioactivity from a C-14 labeled dose of glucosamine is detected in the liver, kidneys, articular cartilage, and other areas.

来源:DrugBank

吸收、分配和排泄

关于饮食中葡萄糖胺的吸收和血清药代动力学信息非常有限，而且在某些情况下，现有数据是相互矛盾的。例如，在一项研究中，对大鼠、狗和人类口服给予了(14)C-葡萄糖胺，在所有情况下，放射性标记都被描述为“有效”吸收，大约4小时后达到血浆峰值。高比例的放射性标记（约35%）通过尿液排出，相似的数量最终随呼出空气排出。另一方面，进行这项实验的实验室在单次口服剂量为100 mg/kg（临床剂量的五倍）后，使用检测限约为14 uM的色谱分析法无法在人类血清中检测到葡萄糖胺的化学量。这表明，在正常推荐剂量（20 mg/kg）后，人类血清中的生物可用葡萄糖胺远低于10 uM。

Information on the absorption and serum pharmacokinetics for dietary glucosamine is very limited, and in some case, the available data are contradictory. For example, in one series of studies, (14)C-glucosamine was given orally to rats, dogs, and humans, and in all cases, the radiolabel was described as "efficiently" absorbed, reaching a plasma peak after about 4 hours. A high percentage of the radiolabel (about 35%) was excreted in the urine, and a similar amount was last in expired air. On the other hand, the laboratory that conducted this experiment was unable to detect chemical amounts of glucosamine in human serum after a single oral dose at 100 mg/kg (five times the clinical dose) using a chromatographic assay with a limit of detection of about 14 uM. This suggests that the bioavailable glucosamine in human serum after the normal recommended dosage (20 mg/kg) is well below 10 uM.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大约90%的葡萄糖胺以葡萄糖胺盐的形式口服给药后从小肠吸收，然后通过门静脉循环输送到肝脏。似乎很大一部分摄入的葡萄糖胺在肝脏通过首次通过代谢被分解。口服摄入后，血清中未检测到游离葡萄糖胺，目前尚不清楚摄入剂量中有多少被人类关节吸收。动物研究观察到关节软骨中有一些吸收。

About 90% of glucosamine administered orally as a glucosamine salt get absorbed from the small intestine, and from there it is transported via the portal circulation to the liver. It appears that a significant fraction of the ingested glucosamine is catabolized by first-pass metabolism in the liver. Free glucosamine is not detected in the serum after oral intake, and it si not presently known how much of an ingested dose is taken up in the joints in humans. Some uptake in the articular cartilage is seen in animal studies.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2940000000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

概述

葡糖胺又称葡萄糖胺、氨基葡糖或2-脱氧氨基葡萄糖，是一种常见的氨基糖，为葡萄糖的一种衍生物。它是通过将葡萄糖分子中第二位碳原子上的羟基被氨基取代而形成的一种化合物。通常一个氢原子会被乙酰基取代，变成N-乙酰葡萄糖胺。在生物体内，葡糖胺很少以游离形式存在，主要作为几丁质、糖蛋白和蛋白聚糖的组成成分。

理化性质

分子式为C6H13NO5（分子量179.17），具有多羟基胺的性质。它通常以聚合物或衍生物的形式存在于甲壳动物、昆虫、霉菌及细菌的细胞壁中。甲壳质是由N-乙酰氨基葡糖组成的缩聚物，在水中的溶解性较高，α-体为晶体状，熔点88℃；β-体则从甲醇中结晶而成，在110℃时分解。

葡糖胺易溶于水、可溶于热甲醇，并微溶于冷甲醇和乙醇，而不溶于乙醚及氯仿。它存在于甲壳多糖、黏蛋白和黏多糖中，是海水、颗粒物及海洋沉积物中的微量有机组分之一。可以从海洋试样中通过水解和阳离子交换柱分离后用光度法测定其含量。

制备方法：由脱水葡萄糖与氨在绝对无水乙醇中反应生成葡糖胺粗品，然后进行水解处理。

天然物质

盐酸葡糖胺是一种天然存在的物质，能够刺激人体产生糖胺聚糖，用于修复和形成软骨。它由葡萄糖和谷氨酰胺这种氨基酸组成，能够促进滑液的产生、关节软骨的修复，并增强结缔组织的合成能力。

葡糖胺是一种天然存在于人体内的氨基酸，其主要作用是形成及修复软骨。随着年龄增长，体内葡糖胺水平逐渐下降，导致软骨退化。补充葡糖胺营养品有助于提升体内的葡糖胺水平。这些补充品通常从螃蟹、龙虾和虾等甲壳海鲜的外壳中提取。

研究表明，补充葡萄糖胺可以缓解轻微至中度骨关节炎患者的疼痛，并可能减缓其软骨损伤的速度。这是因为葡糖胺是合成糖胺聚糖的前体物质，而后者对修复关节软骨组织至关重要。人体需要这些糖胺聚糖来制造蛋白聚糖，这是一种以蛋白质和糖为基础的类似胶泥的物质。

生物活性

葡糖胺（2-氨基-2-脱氧-D-葡萄糖）是一种重要的氨基糖，在生化合成糖基化蛋白和脂质方面具有重要作用。它常用于治疗骨关节炎。

化学性质上，葡糖胺为白色结晶或结晶性粉末。 用途广泛应用于卫生药品、保健食品及美容化妆品的生产中，对提高人类活动生命率、促进人体合成生命的组织生长等有着重要的保健作用。

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-amino glucose 在 phosphate buffer 、 次碘(I)酸 作用下， 以 水 为溶剂， 生成 碘仿
  参考文献：
  名称：

  含碘水消毒和氧化过程中碘三卤甲烷的形成

  摘要：

  在含碘饮用水的氧化处理过程中，碘代三卤甲烷 (I-THM) （如碘仿 (CHI3)）的形成可能会导致味道和气味问题。I-THM 由次碘酸 (HOI) 与天然有机物反应形成。HOI 是由天然存在的碘化物 (I-) 通过臭氧、氯或氯胺氧化而迅速形成的。测量了 HOI 与有机模型化合物的反应动力学以及由此产生的 CHI3 形成。发现取代的苯酚、苯酚和较小程度的 α-甲基羰基化合物对 HOI 具有反应性，并且还会产生 CHI3。间苯二酚（间羟基苯酚）的 CHI3 产率最高。还在用臭氧、氯或氯胺氧化处理的天然水中测量了 I-THM 形成的动力学。使用臭氧时，未检测到 I-THM，≥90% 的 I- 转化为 IO3-。氯导致 IO3- 和 I-THM 的形成。随着氯剂量的增加，CHI3 形成...

  DOI：

  10.1021/es9914590
• 作为产物：
  描述：

  果糖 在 氨 作用下， 反应 48.0h， 生成 2-deoxy-2-amino glucose
  参考文献：
  名称：

  Preparation of glucosamine

  摘要：

  揭示了一种从果糖和氨或氨源（如铵化合物）制备葡萄糖胺酸盐的过程，方法是在存在（i）约25至100重量百分比水和75至0重量百分比惰性有机亲水溶剂的溶剂中，以约1至6的aWWpH或SWpH条件下，将果糖和氨或氨源接触；或者（ii）在存在约75至100重量百分比惰性有机亲水溶剂和0至25重量百分比水的溶剂中，以约1至10的aWWpH或SWpH条件下进行。该过程还会产生一种甘露胺酸盐作为副产品。

  公开号：

  US20070088157A1
• 作为试剂：
  描述：

  吲哚 、 sodium 4-fluorobenzenesulfinate 在 碘化铵 、 2-deoxy-2-amino glucose 、 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以89%的产率得到3-((4-fluorophenyl)thio)-1H-indole
  参考文献：
  名称：

  铜催化D-葡糖胺促进吲哚区域选择性亚硫烷基化的组合实验/理论研究

  摘要：

  提出了结合铜催化的亚磺酸钠对D-氨基葡萄糖促进的C3位吲哚亚磺酰基化的实验/理论研究。吲哚的C3-亚磺酰化显示出良好的官能团耐受性和产率。3-I-吲哚被确定为催化循环中的关键中间体。[Cu（DMSO）2] 2+的催化作用已通过量子化学计算得到解决。在[Cu（DMSO）2] 2+与吲哚的相互作用中，配合物[Cu（DMSO）2] 2+从吲哚的C3提取氢。揭示了吲哚选择性CH键活化的电子起源。

  DOI：

  10.1039/c7nj02784b

文献信息

• Low molecular weight polyglucosamines and polygalactosamines
  申请人：Sabesan Subramaniam

  公开号：US20060286149A1

  公开（公告）日：2006-12-21

  Compositions containing enriched populations of beta linked low molecular weight polymers of galactosamine and glucosamine are provided. The compositions are useful, for example, as antibacterial additives for food and other edible applications, as precursors for synthesizing other biologically active molecules related to chitin/chitosan oligomers, and/or as pharmaceutical compounds.

  提供了含有富集的β连接低分子量聚合物的半乳糖胺和葡萄糖胺的组合物。这些组合物可用作食品和其他可食用应用的抗菌添加剂，例如，作为合成与壳聚糖/壳寡糖相关的其他生物活性分子的前体，和/或作为药用化合物。
• [EN] SYNTHETIC OLIGOGLUCOSAMINES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD<br/>[FR] OLIGOGLUCOSAMINES SYNTHÉTIQUES POUR L'AMÉLIORATION DE LA CROISSANCE ET DU RENDEMENT DE VÉGÉTAUX
  申请人：DU PONT

  公开号：WO2015130893A1

  公开（公告）日：2015-09-03

  The disclosure provides formulations comprising synthetic oligoglucosamines and methods for improving plant growth and crop yield therewith. These formulations may be applied to propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield.

  该披露提供了包含合成寡聚葡聚糖胺的配方，以及利用这些配方改善植物生长和作物产量的方法。这些配方可以应用于繁殖材料，包括种子和其他可再生植物部分，如插条、球茎、根茎和块茎。它们也可以应用于叶片或土壤，无论是在种植繁殖材料之前还是之后。这些应用可以单独进行，也可以与杀菌剂、杀虫剂、线虫杀灭剂和其他用于改善植物生长和作物产量的农业药剂结合使用。
• Study of the stereoselectivity of 2-azido-2-deoxyglucosyl donors: protecting group effects
  作者：George Ngoje、Zhitao Li

  DOI：10.1039/c3ob26994a

  日期：——

  A series of tolyl 2-azido-2-deoxy-thio-glucoside donors with different combinations of protecting groups were prepared. These donors were used in glycosylation reactions to test the correlations between the stereoselectivity and the pattern of the protecting groups. Acetyl groups showed a position dependent stereo-directing effect. A remote participating mechanism is proposed to explain the observed results.

  制备了一系列具有不同保护基组合的对甲苯基2-叠氮-2-脱氧硫代葡糖供体。这些供体被用于糖基化反应，以测试立体选择性与保护基模式之间的相关性。乙酰基表现出位置依赖性的立体导向效应。提出了一种远程参与机制，以解释观察到的结果。
• Derivatives of Salarin A, Salarin C and Tulearin A—Fascaplysinopsis sp. Metabolites
  作者：Lee Zur、Ashgan Bishara、Maurice Aknin、Drorit Neumann、Nathalie Ben-Califa、Yoel Kashman

  DOI：10.3390/md11114487

  日期：——

  Derivatives of salarin A, salarin C and tulearin A, three new cytotoxic sponge derived nitrogenous macrolides, were prepared and bio-evaluated as inhibitors of K562 leukemia cells. Interesting preliminary SAR (structure activity relationship) information was obtained from the products. The most sensitive functionalities were the 16,17-vinyl epoxide in both salarins, the triacylamino group in salarin A and the oxazole in salarin C (less sensitive). Regioselectivity of reactions was also found for tulearin A.

  从海绵中提取的三种新的细胞毒性含氮大环内酯——salarin A、salarin C和tulearin A的衍生物，被制备并生物评价为K562白血病细胞的抑制剂。从这些产物中获得了有趣的初步的结构活性关系（SAR）信息。其中最敏感的功能基团包括salarin中16,17位的乙烯基环氧化物、salarin A中的三酰氨基团以及salarin C中的噁唑环（较不敏感）。tulearin A的反应还表现出区域选择性。
• Synthesis and cytotoxicity evaluation of glycosidic derivatives of lawsone against breast cancer cell lines
  作者：Flaviano M. Ottoni、Eliza R. Gomes、Rodrigo M. Pádua、Mônica C. Oliveira、Izabella T. Silva、Ricardo J. Alves

  DOI：10.1016/j.bmcl.2019.126817

  日期：2020.1

  anti-hormonal therapy, the development of new antineoplastic drugs is necessary. Lawsone (2-hydroxy-1,4-naphtoquinone) is a natural bioactive naphtoquinone displaying a range of activities, with dozens of derivatives described in the literature, including some glycosides possessing antitumor activity. Here, a series of glycosides of lawsone are reported for the first time and all compounds displayed good activity

  乳腺癌是女性中发病率最高且致命的癌症类型，到2020年，全世界估计有200万例新病例，其中60万人死亡。由于并非所有类型的乳腺癌都对抗激素疗法产生反应，因此有必要开发新的抗肿瘤药。Lawsone（2-hydroxy-1,4-naphtoquinone）是一种天然的生物活性萘醌，具有多种活性，文献中描述了数十种衍生物，包括一些具有抗肿瘤活性的糖苷。在这里，首次报道了一系列的Lawsone苷，并且所有化合物都显示出对SKBR-3细胞系的良好活性，IC50低于10 µM。最有希望的衍生物是衍生自过乙酰化d-葡萄糖的糖基三唑（11），它对SKBR-3具有更好的细胞毒性（IC50 = 0.78 µM），对这种肿瘤细胞具有最高的选择性（SI> 20）。这项工作中描述的所有化合物都比劳森酮更具活性，表明碳水化合物和糖基三唑部分对于活性很重要。