2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide | 69435-07-0

• 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: 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide
• 英文别名: 1-tetra-O-acetyl-β-D-glucopyranosyl-4-phenyl thiosemicarbazide；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(anilinocarbamothioylamino)oxan-2-yl]methyl acetate
• CAS: 69435-07-0
• 化学式: C₂₁H₂₇N₃O₉S
• 分子量: 497.526
• InChiKey: QWRRXDIBUUXJJT-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  183
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide 在 氨 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Jadhao, D.B.; Berad, B.N.; Paranjpe, M.G., Journal of the Indian Chemical Society, 1993, vol. 70, # 10, p. 823 - 826

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 、 苯肼 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide
  参考文献：
  名称：

  Syntheses and evaluation of glucosyl aryl thiosemicarbazide and glucosyl thiosemicarbazone derivatives as antioxidant and anti-dyslipidemic agents

  摘要：

  A series of N-per-O-acetyl-glucosyl arylthiosemicarbazide and thiosemicarbazone derivatives have been synthesized and evaluated for their in vivo anti-dyslipidemic and in vitro antioxidant activities. Among 16 compounds tested, 3 compounds showed potent anti-dyslipidemic activity and 6 compounds showed potent antioxidant and scavenger of oxygen free radicals activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.070

文献信息

• Studies on nucleoside analogs. XXI. A convenient synthesis of 1,2,4-triazole-5-thione glycosides.
  作者：HARUO OGURA、HIROSHI TAKAHASHI、OSAMU SATO

  DOI：10.1248/cpb.29.2188

  日期：——

  The reaction of glycosyl isothiocyanates (1a-c) with acyl or aroyl hydrazine, followed by treatment with Ac2O-H3PO4, afforded 1, 2, 4-triazole-5-thione glycosides (20a, 21a-c, 22a) in fair yields. Attempts to prepare 1, 2, 4-triazole glycoside analogs with acetic anhydride or sodium methoxide failed. The reaction of glycosyl-2-(phenyl-or pyrid-2-ylhydrazine) thiocarboxamides (6a, 7a) with phosgene in pyridine or triethylamine gave thiadiazole-5-thiones (8a, 9a) instead of 1, 2, 4-triazole glycosides.

  糖基异硫氰酸酯 (1a-c) 与酰基或芳酰肼反应，然后用 Ac2O-H3PO4 处理，以良好的收率得到 1,2,4-三唑-5-硫酮糖苷 (20a, 21a-c, 22a)。用乙酸酐或甲醇钠制备1,2,4-三唑糖苷类似物的尝试失败了。糖基-2-(苯基-或吡啶-2-基肼)硫代甲酰胺(6a, 7a)与光气在吡啶或三乙胺中反应生成噻二唑-5-硫酮(8a, 9a)而不是1,2,4-三唑糖苷。
• Garnaik, Bama K.; Behera, Rajani K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1157 - 1158
  作者：Garnaik, Bama K.、Behera, Rajani K.

  DOI：——

  日期：——
• Syntheses and evaluation of glucosyl aryl thiosemicarbazide and glucosyl thiosemicarbazone derivatives as antioxidant and anti-dyslipidemic agents
  作者：Samir Ghosh、Anup Kumar Misra、Gitika Bhatia、M.M. Khan、A.K. Khanna

  DOI：10.1016/j.bmcl.2008.11.070

  日期：2009.1

  A series of N-per-O-acetyl-glucosyl arylthiosemicarbazide and thiosemicarbazone derivatives have been synthesized and evaluated for their in vivo anti-dyslipidemic and in vitro antioxidant activities. Among 16 compounds tested, 3 compounds showed potent anti-dyslipidemic activity and 6 compounds showed potent antioxidant and scavenger of oxygen free radicals activity. (C) 2008 Elsevier Ltd. All rights reserved.
• Jadhao, D.B.; Berad, B.N.; Paranjpe, M.G., Journal of the Indian Chemical Society, 1993, vol. 70, # 10, p. 823 - 826
  作者：Jadhao, D.B.、Berad, B.N.、Paranjpe, M.G.

  DOI：——

  日期：——