4-amino-3-(D-glucoheptonic-hexitol-1-yl)-1H-1,2,4-triazole-5-thione | 219474-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-3-(D-glucoheptonic-hexitol-1-yl)-1H-1,2,4-triazole-5-thione
• 英文别名: 4-amino-3-[(1S,2S,3R,4R,5R)-1,2,3,4,5,6-hexahydroxyhexyl]-1H-1,2,4-triazole-5-thione
• CAS: 219474-93-8
• 化学式: C₈H₁₆N₄O₆S
• 分子量: 296.304
• InChiKey: HPAGGZDTANKBJV-VFUOTHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-amino-3-(D-glucoheptonic-hexitol-1-yl)-1H-1,2,4-triazole-5-thione 、 2-溴-2',4'-二氟苯乙酮 以 乙醇 为溶剂， 反应 4.0h， 以89%的产率得到6-(2,4-difluorophenyl)-3-(D-glucoheptonic-hexitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  6-芳基-3-(D-glucoheptonic-hexitol-1-yl)-7H-1,2,4-三唑并[3,4-b][1,3,4]噻二嗪的合成及生物活性

  摘要：

  一系列新型 6-aryl-3-(D-glucoheptonic-hexitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4] 噻二嗪 (2a–2j) ) 通过 4-amino-5-mercapto-3-(D-glucoheptonic-hexitol-1-yl)-1,2,4-triazole (1) 与取代的 ω-brom 的反应以高产率合成- 苯乙酮。化合物的结构通过元素分析、IR、1H NMR、13C NMR和MS确定。大多数具有高植物生长调节活性。

  DOI：

  10.3184/030823407x210901
• 作为产物：
  描述：

  硫代卡巴肼 、 葡庚糖酸内酯 在 吡啶 作用下， 反应 4.0h， 以80%的产率得到4-amino-3-(D-glucoheptonic-hexitol-1-yl)-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some Novel Schiff’s Bases from 1,2,4-Triazole

  摘要：

  我们从 4-氨基-3-(D-glucoheptonic-hexitol-1-yl)-1H-1,2,4-三唑-5-硫酮合成了一些新型希夫碱。通过在 1,2,4-三唑的 3-位上连接 D-葡萄糖庚基-1-己糖醇残基，标题化合物的溶解性得到了极大的改善。所有产物都通过元素分析、红外光谱、1H-NMR、13C-NMR 和质谱进行了表征。对标题化合物的植物生长调节作用进行了研究。从生物活性结果来看，大多数化合物表现出弱到中等的活性。

  DOI：

  10.3390/12061202

文献信息

• NOVEL SYNTHESIS OF<i>seco</i>TYPE OF ACYCLO<i>C</i>-NUCLEOSIDES OF 1,2,4-TRIAZOLE AND 1,2,4-TRIAZOLO[3,4-b][1,3,4]THIADIAZINE
  作者：El Sayed H. El Ashry、Laila F. Awad

  DOI：10.1081/ncn-100001440

  日期：2001.2.26

  -mercapto-1,2,4-triazole (12) with phenacylbromide (11) afforded the corresponding 3-(D-gluco-, D-galacto-pentitol-1-yl) and 3-(D-glycero-D-gulo-hexitol-1-yl)-6-phenyl-7H-1,2,4- triazolo[3,4-b][1,3,4] thiadiazines (15, 16, and 17). Acetylation of 15–17 gave the penta- and hexa-O-acetyl derivatives 18–20, respectively. The structures were confirmed by using 1H, 13C, and 2D NMR spectra, DQFCOSY, HMQC

  Seco C-核苷3-（1,2,3,4,5-penta-O-乙酰基-D-葡萄糖-和D-半乳糖-戊糖醇-1-基）-1H-1,2,4-三唑（在一锅中通过对4-氨基-3-（D-葡萄糖和D-半乳糖-戊糖醇-1-基）-5-巯基-1,2,4-三唑（ 1和2），分别在正磷酸中使用亚硝酸钠，然后进行乙酰化。1，2，和4-氨基-3-（D-甘油-D-果糖己糖醇-1-基）-5-巯基-1,2,4-三唑（12）与苯乙溴（11）的缩合反应相应的3-（D-葡萄糖基，D-半乳糖基戊糖醇-1-基）和3-（D-甘油-D-gulo-己糖醇-1-基）-6-苯基-7H-1,2,4- triazolo [3,4-b] [1,3,4]噻二嗪（15、16和17）。乙酰化15-17分别生成五-和六-O-乙酰基衍生物18-20。通过使用1H，13C和2D NMR光谱，DQFCOSY，HMQC和HMBC实验来确认结构。
• Synthesis and conformational analysis of seco C-nucleosides and their diseco double-headed analogues of the 1,2,4-triazole, 1,2,4-triazolo[3,4-b]1,3,4-thiadiazole1Parts of this work were presented at 19th International Carbohydrate Symposium, San Diego, CA, USA, August 1998 and XIII International Round Table, Nucleosides, Nucleotides and their Biological Applications, Montpellier, France, September 1998.1
  作者：Laila F. Awad、El Sayed H.El Ashry

  DOI：10.1016/s0008-6215(98)00205-5

  日期：1998.11

  Reaction of D-glucono- (1) or D-galactono- (2) 1,5-lactones and D-glycero-D-guloheptonic-1,4-lactone (11) with thiocarbohydrazide (3) afforded the seco C-nucleosides 4-amino-3-(D-gluco- (4) or D-galacto- (5) pentitol-1-yl)-5-mercapto-1,2,4-triazoles and 4-amino-3-(D-glycero-D-gulo-hexitol-1-yl)-5-mercapto-1,2,4-triazole (12). Their conversions to the 3-(1,2,3,4,5-penta-O-acyl-D-gluco- (7 and 9) or the D-galacto (8 and 10) pentitol-1-yl)-6-substituted 1,2,4-triazolo[3,4-b]1,3,4-thiadiazole and 3-(1,2,3,4,5,6-hexa-O-acetyl-D-glycero-D-gulohexitol-1-yl)-6-methyl-1,2,4-triazolo[3,4-b]1,3,4-thiadiazole (13) were achieved under acylative conditions. Reaction of diethyl galactrate (17) with 3 gave 1,4-bis (4-amino-5-mercapto-1,2,4-triazol-3-yl)-galacto-tetritol (18), which upon reaction with acetic anhydride gave 1,4-bis(6-methyl-1,2,4-triazolo[3,4-b]1,3,4-thiadiazol-3-yl)-1,2,3,4-tetra-O-acetyl-galacto-tetritol (19). When the tetra-O-acetylgalactaric acid (15) was used instead of 17, the attack of 3 had taken place on the ester group rather than the carboxylic group, whereby 16 was obtained rather than the tetra-O-acetyl derivative of 18. The structures were confirmed by using H-1, C-13 and 2D NMR spectra (DQFCOSY and HMQC) experiments. The vicinal coupling constants were used to deduce the favored conformations. (C) 1998 Elsevier Science Ltd. All rights reserved.