4-amino-3-(D-gluco-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole | 219474-86-9

• 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-gluco-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole
• 英文别名: 4-amino-3-(D-gluco-pentitol-1-yl)-5-mercapto-1,2,4-triazoles；4-amino-3-(D-gluco-pentitol-1-yl)-5-mercapto-1,2,4-triazole；4-amino-3-(D-glucopentitol-1-yl)-5-mercapto-1,2,4-triazole；4-amino-5-mercapto-3-(D-glucopentitol-1-yl)-1,2,4-triazole；4-amino-3-[(1S,2R,3R,4R)-1,2,3,4,5-pentahydroxypentyl]-1H-1,2,4-triazole-5-thione
• CAS: 219474-86-9
• 化学式: C₇H₁₄N₄O₅S
• 分子量: 266.278
• InChiKey: SVMZQMVXSWCYAB-SQOUGZDYSA-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-gluco-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole 在 磷酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-(D-gluco-pentitol-1-yl)-4H-1,2,4-triazole
  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 、 葡萄糖酸内酯 在 吡啶 作用下， 以88%的产率得到4-amino-3-(D-gluco-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole
  参考文献：
  名称：

  Microwave-Assisted Organic Synthesis of 3-(D-gluco- Pentitol-1-Yl)-1H-1,2,4-Triazole

  摘要：

  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.

  DOI：

  10.1080/15257770500544545
• 作为试剂：
  描述：

  对硝基苯-α-D-葡萄糖吡喃苷 在 sodium acetate buffer 、 mouse hepatic α-glucosidase 、 4-amino-3-(D-gluco-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole 作用下， 以 水 为溶剂， 反应 0.5h， 生成 对硝基苯酚
  参考文献：
  名称：

  INHIBITION OF SOME HEPATIC GLYCOSIDASES BY THE DISECO NUCLEOSIDE, 4-AMINO-3-(D-GLUCOPENTITOL-1-YL)- 5-MERCAPTO-1,2,4-TRIAZOLE AND ITS 3-METHYL ANALOG

  摘要：

  The in vivo and in vitro effects of 4-amino-3-(D-glucopentitol-1-yl)-5-mercapto-1,2,4-triazole and its 3-methyl analogue on alpha- and beta-glucosidases, beta-glucuronidase as well as a-amylase have been investigated. alpha-Glucosidase is the enzyme that is markedly affected in vivo and in vitro in a dose-dependent manner. The compounds showed a reversible inhibition of a competitive type for alpha-glucosidase. Moreover, they exert a relatively potent inhibition on alpha-glucosidase with a K-i magnitude of 3.6 x 10(-4), 9.5 x 10(-5) M.

  DOI：

  10.1081/ncn-120015726

文献信息

• SYNTHESIS OF 6-ARYL-3-(<scp>d</scp>-GLUCO-PENTITOL-1-YL)-7<i>H</i>-1,2,4-TRIAZOLO- [3,4-b][1,3,4]THIADIAZINES
  作者：Yi Xiong、Lixue Zhang、Anjiang Zhang、Duanjun Xu

  DOI：10.1081/scc-120014776

  日期：2002.1

  ABSTRACT Some 6-aryl-3-(d-gluco-pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b]- [1,3,4]thiadiazines are readily accessible in high yields by reaction of 4-amino-5-mercapto-3-(d-gluco-pentitol-1-yl)-1,2,4-triazole with substituted ω-bromoacetophenones.

  摘要 一些 6-aryl-3-(d-gluco-pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b]-[1,3,4]thiadiaazines 很容易在高通过 4-amino-5-mercapto-3-(d-gluco-pentitol-1-yl)-1,2,4-triazole 与取代的 ω-bromoacetophenones 反应产生。
• 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。
• 1H and13C NMR study of 5-substituted-4- (arylidene)amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 6-aryl-3-(D-gluco- pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b] [1,3,4]thiadiazines
  作者：Anjiang Zhang、Lixue Zhang、Xinxiang Lei

  DOI：10.1002/mrc.1829

  日期：2006.8

  Five 5‐substituted‐4‐(arylidene)amino‐2,4‐dihydro‐3H‐1, 2,4‐triazole‐3‐thiones (2a–2e) and seven 6‐aryl‐3‐(D‐gluco‐pentitol‐1‐yl)‐7H‐1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazines (3a–3g) were synthesized. The complete 1H and 13C NMR chemical shift assignments were analyzed on one‐ and two‐dimensional NMR techniques, including DEPT, NOE‐DIF, COSY, gHMBC, and gHSQC. Copyright © 2006 John Wiley & Sons, Ltd

  五个 5-取代-4-(亚芳基)氨基-2,4-二氢-3H-1, 2,4-三唑-3-硫酮 (2a-2e) 和七个 6-芳基-3-(D-葡萄糖-戊糖醇)合成了-1-基)-7H-1,2,4-三唑并[3,4-b][1,3,4]噻二嗪(3a-3g)。完整的 1H 和 13C NMR 化学位移分配在一维和二维 NMR 技术上进行分析，包括 DEPT、NOE-DIF、COSY、gHMBC 和 gHSQC。版权所有 © 2006 John Wiley & Sons, Ltd.
• A Novel Approach for the Synthesis of<i>seco</i>C-Nucleoside Analogues
  作者：Laila F. Awad、El Sayed H. El Ashry

  DOI：10.1080/15257779908041493

  日期：1999.4

  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.
• 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.