4-amino-3-(D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazole | 219474-87-0

• 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-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazole
• 英文别名: 4-amino-3-(D-galacto-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole；4-amino-3-[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl]-1H-1,2,4-triazole-5-thione
• CAS: 219474-87-0
• 化学式: C₇H₁₄N₄O₅S
• 分子量: 266.278
• InChiKey: SVMZQMVXSWCYAB-MGCNEYSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-3-(D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazole 在 磷酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  1,2,4-三唑的山高C-核苷类似物。

  摘要：

  Seco C-核苷3-（1,2,3,4,5-戊-O-乙酰基-D-葡萄糖-和D-半乳糖-戊醇-1-基）-1H-1,2,4-三唑（一锅中通过4-氨基-3-（D-葡萄糖和D-半乳糖戊糖醇-1-基）-5-巯基-1,2,4-三唑的脱氨基和脱硫反应获得6和7）和2）分别使用亚磷酸钠的正磷酸溶液和随后的乙酰化反应。通过使用1H，13C和2D NMR光谱，DQFCOSY，HMQC和HMBC实验来确认结构。从质子的邻偶耦合常数推导了有利的构象结构。

  DOI：

  10.1081/ncn-100002455
• 作为产物：
  描述：

  硫代卡巴肼 、 D-galactono-1,5-lactone 以 吡啶 为溶剂， 生成 4-amino-3-(D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazole
  参考文献：
  名称：

  A Novel Approach for the Synthesis ofsecoC-Nucleoside Analogues

  摘要：

  The synthesis of 4-amino-3-(D-gluco- or D-galacto-pentitoi-1.yl)-5-mercapto-1,2,4-triazoles and their conversion to the respective 6-methyl-3-(1,2,3,4,5-penta-O-acetyl-pentitol-1-yl)1,2,4-triazolo[3,4-b] 1,3,4-thiadiazoles have been achieved. The vicinal coupling constants were used to deduce the favored conformations.

  DOI：

  10.1080/15257779908041493

文献信息

• Synthesis and Biological Activity of Some Novel Derivatives of 4-Amino-3-(D-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole
  作者：Jian-yu Jin、Li-xue Zhang、An-jiang Zhang、Xin-Xiang Lei、Jiang-Hai Zhu

  DOI：10.3390/12081596

  日期：——

  To discover new 1,2,4-triazole derivatives which may possess significant biological activities, we synthesized a series of novel 6-aryl-3-(D-galactopentitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines and 4-(arylmethylidene)amino-5-(D-galactopentitol-1-yl)-3-mercapto-4H-1,2,4-triazoles from 4-amino-3-(D-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole. All the title compounds were characterized

  为了发现可能具有重要生物活性的新型 1,2,4-三唑衍生物，我们合成了一系列新型 6-aryl-3- (D-galactopentitol-1-yl) -7H-1,2,4-triazolo [ 3,4-b] [1,3,4] 噻二嗪和 4-（芳基亚甲基）氨基-5-（D-半乳糖戊醇-1-基）-3-巯基-4H-1,2,4-三唑来自 4-氨基-3- (D-galactopentitol-1-yl) -5-mercapto-1,2,4-triazole。所有标题化合物均通过元素分析、IR、1H-和 13C-NMR 表征。植物生长调节活性试验表明，这些化合物对萝卜和小麦的生长有显着影响。
• 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。
• Microwave-Assisted Organic Synthesis of 3-(D-<i>gluco-</i> Pentitol-1-Yl)-1<i>H</i>-1,2,4-Triazole
  作者：E. S. H. El Ashry、L. F. Awad、H. M. Abdel Hamid、A. I. Atta

  DOI：10.1080/15257770500544545

  日期：2006.4.1

  The condensation of D-glucono- and the D-galactono-1,5-lactone and thiocarbohydrazide to give 3-(D-alditol-1-yl)-4-amino-5-mercapto-1,2,4-triazoles 4 and 5 is accelerated by the use of microwave-assisted organic reaction (MAOS). The deamination and dethiolation of compound 4 to give 6 was also accelerated by the use of MAOS. Condensation of 4 and 5 with p-nitrobenzaldehyde afforded Schiff bases 8 and 9, respectively, within 4 min under microwave irradiation (MWI), whereas with ethyl chloroacetate the thioalkylated products 14 and 15 were obtained in 8 min. The structures of the synthesized compounds were confirmed by H-1 NMR, 2D NMR, and mass spectra.
• MICROWAVE IRRADIATION FOR ACCELERATING THE SYNTHESIS OF ACYCLONUCLEOSIDES OF 1,2,4-TRIAZOLE
  作者：E. S. H. El Ashry、L. F. Awad、H. M. Abdel Hamid、A. I. Atta

  DOI：10.1081/ncn-200059975

  日期：2005.4.1

  The 3-(D-alditol-1-yl)-4-amino-5-mercapto- 1,2,4-triazoles 4 and 5 can be successfully prepared using microwave irradiation. Condensation of 4 and 5 with p-nitrobenzaldehyde afforded Schiff bases 6 and 7, respectively. Reaction 4 and 5 with ethylchloroacelate gave the corresponding alkylated products 10 and 11 Better yields and much less time were the characteristic features of using the microwave heating over the conventional one. The structure of the prepared compounds was confirmed by H-1-NMR, 2D-NMR and mass spectra.
• 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.