2-(β-D-galactopyranosyl)hydrazinecarbothioamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(β-D-galactopyranosyl)hydrazinecarbothioamide
• 英文别名: β-D-galactopyranosylthiosemicarbazone；β-D-galactose thiosemicarbazone；[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]thiourea
• 化学式: C₇H₁₅N₃O₅S
• 分子量: 253.279
• InChiKey: YMJWCYLPMHAALV-FPRJBGLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  172
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 2-(β-D-galactopyranosyl)hydrazinecarbothioamide 反应 0.08h， 以87%的产率得到methyl (2E)-2-(4-oxo-2-((β-D-galactopyranosyl)hydrazono)thiazolidin-5-ylidene)acetate
  参考文献：
  名称：

  Facile one-pot synthesis of sugar–thiazolidinone derivatives

  摘要：

  一种简单、高效、经济的方法被描述，用于通过一锅法反应d-半乳糖、d-葡萄糖和d-甘露醇的相应硫脲半羧酸盐，在二甲基或二乙基乙炔二羧酸的存在下合成一系列糖-噻唑烷衍生物。两种不同的方法被使用，并在两种情况下获得高产率：（A）在EtOAC-H2O中，在常温下，（B）在无溶剂条件下进行微波辐射。

  DOI：

  10.1139/v11-123
• 作为产物：
  描述：

  β-半乳糖苷酶 、 氨基硫脲 以 乙醇 为溶剂， 反应 8.0h， 生成 2-(β-D-galactopyranosyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Facile one-pot synthesis of sugar–thiazolidinone derivatives

  摘要：

  一种简单、高效、经济的方法被描述，用于通过一锅法反应d-半乳糖、d-葡萄糖和d-甘露醇的相应硫脲半羧酸盐，在二甲基或二乙基乙炔二羧酸的存在下合成一系列糖-噻唑烷衍生物。两种不同的方法被使用，并在两种情况下获得高产率：（A）在EtOAC-H2O中，在常温下，（B）在无溶剂条件下进行微波辐射。

  DOI：

  10.1139/v11-123

文献信息

• Synthesis of New Gluco-, Galacto-, and Mannopyranosylthiazoles, Thiazolidinones, and Pyranosylthiazlidin-4-ones from Sugar Thiosemicarbazone Derivatives
  作者：Ali Darehkordi、Mahin Ramezani、Reza Ranjbar-Karimi

  DOI：10.1002/hc.21083

  日期：2013.5

  A new series of potentially biological active derivatives, namely alkyl-2-((4-oxo-2-(phenylimino)-3-(β-d-pyranosyl-2-ylamino)thiazolidine-5-ylidene)acetate (5a–f), 4-(4-bromophenyl)thiazol-2(3H)-ylidene)hydrazinyl)-β-d-pyranosyl (4a–c), and 5-(4-bromophenyl)-2-(phenylimino)-3-(β-d-pyranosyl-2-ylamino)thiazolidine-4-one (6) were synthesized via a reaction of the sugar thiosemicarbazone derivatives with

  一系列具有潜在生物活性的新衍生物，即烷基-2-((4-oxo-2-(phenylimino)-3-(β-d-pyranosyl-2-ylamino)thiazolidine-5-ylidene)acetate (5a–f )、4-(4-溴苯基)噻唑-2(3H)-亚基)肼基)-β-d-吡喃糖基(4a-c)和5-(4-溴苯基)-2-(苯基亚氨基)-3-( β-d-吡喃糖基-2-基氨基)噻唑烷-4-酮 (6) 分别通过糖缩氨基硫脲衍生物与 2,4'-二溴苯乙酮、二烷基乙炔二羧酸酯和溴乙酸乙酯的反应合成。通过光谱方法（FT-IR、1H NMR、13C NMR和2D NMR）和元素分析确定合成化合物的结构。此外，回流和环境温度下的各种溶剂对糖缩氨基脲与 2,4'二溴苯乙酮、乙炔二羧酸二乙酯、并研究了乙炔二羧酸二甲酯。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:200–207
• Chemical entities that kill senescent cells for use in treating age-related disease
  申请人：Unity Biotechnology, Inc.

  公开号：US10195213B2

  公开（公告）日：2019-02-05

  Disclosed herein are compounds that are effective for treatment of various disease states associated with senescence. The disclosed compounds can be used to eliminate senescent cells for disease treatment. The dosing of the compounds includes both single administration and regimens of cycling dosages.

  本文公开的化合物可有效治疗与衰老有关的各种疾病状态。所公开的化合物可用于消除衰老细胞以治疗疾病。化合物的给药方式包括单次给药和循环给药。
• Behavior of free sugar thiosemicarbazones toward heterocyclization reactions
  作者：Miriam A. Martins Alho、Norma B. D'Accorso

  DOI：10.1016/s0008-6215(00)00127-0

  日期：2000.10

  The heterocyclization reaction on thiosemicarbazones having the D-galacto, D-gluco and D-manno configuration was studied. We applied two different acetylating conditions, and the reaction products obtained were identified, spectroscopically characterized, and conformationally analyzed. Using experimental data, we discuss a possible mechanistic pathway for heterocyclization and evaluate the influence of several factors, including starting material configuration, pH of reaction medium, and reaction time.
• COMPOUNDS AND THERAPEUTIC USES
  申请人：Unity Biotechnology, Inc.

  公开号：US20170281649A1

  公开（公告）日：2017-10-05

  Disclosed herein are compounds that are effective for treatment of various disease states associated with senescence. The disclosed compounds can be used to eliminate senescent cells for disease treatment. The dosing of the compounds includes both single administration and regimens of cycling dosages.
• Facile one-pot synthesis of sugar–thiazolidinone derivatives
  作者：Ali Darehkordi、Kazem Saidi、Somayeh Ghazi

  DOI：10.1139/v11-123

  日期：2011.11

  A simple, efficient, and cost-effective method for the synthesis of a series of sugar–thiazolidinone derivatives by a one-pot reaction of the corresponding thiosemicarbazone of d-galactose, d-glucose, and d-mannose compounds in the presence of dimethyl or diethyl acetylenedicarboxylate is described. Two different methods were used and high yields were obtained in both cases: (A) in EtOAC–H₂O at an ambient temperature and (B) microwave irradiation under solvent-free conditions.

  一种简单、高效、经济的方法被描述，用于通过一锅法反应d-半乳糖、d-葡萄糖和d-甘露醇的相应硫脲半羧酸盐，在二甲基或二乙基乙炔二羧酸的存在下合成一系列糖-噻唑烷衍生物。两种不同的方法被使用，并在两种情况下获得高产率：（A）在EtOAC-H2O中，在常温下，（B）在无溶剂条件下进行微波辐射。