N-tetra-O-acetyl-β-D-glucopyranosyl isocyanodichloride | 104910-44-3

• 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: N-tetra-O-acetyl-β-D-glucopyranosyl isocyanodichloride
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(dichloromethylideneamino)oxan-2-yl]methyl acetate
• CAS: 104910-44-3
• 化学式: C₁₅H₁₉Cl₂NO₉
• 分子量: 428.223
• InChiKey: CBWANCLXFDLWMM-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126.79
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-tetra-O-acetyl-β-D-glucopyranosyl isocyanodichloride 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以60%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-chlorotetrazol-1-yl)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Hassel, Tillmann; Mueller, Hanns Peter, Angewandte Chemie, 1987, vol. 99, # 4, p. 368 - 369

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 在 氯 作用下， 生成 N-tetra-O-acetyl-β-D-glucopyranosyl isocyanodichloride
  参考文献：
  名称：

  通过碳-硫键形成合成和表征 N-葡萄糖基化的二硫二氮杂衍生物

  摘要：

  摘要 通过 N-四-O-乙酰基-β-d 反应合成了新型 4,7-双(芳氨基)-2-四-O-乙酰基-β-d-吡喃葡萄糖基亚氨基-1,3,5,6-二硫氮杂-吡喃葡萄糖基异氰二氯化物与 1,6-二芳基-2,5-二硫代-双-脲，不使用任何催化剂。因此，探索了通过碳硫键形成合成含有两个硫和两个氮原子的 7 元杂环。这些新化合物的化学结构通过 IR、1H NMR、13C NMR、质谱和元素分析得到阐明。

  DOI：

  10.1515/hc-2015-0093

文献信息

• Synthesis and Molecular Docking Studies of Glucose-linked Isonicotinoyl- 1,3,4-Thiadiazolidines as Antitubercular Agents
  作者：Snehal A. Chavan、Avinash G. Ulhe、Baliram N. Berad、Rupesh V. Chikhale

  DOI：10.2174/1570178614666170608130326

  日期：2017.12.11

  Background: The recent emergence of multidrug-resistant strains of M. tuberculosis that are resistant to two major effective drugs, viz. isoniazid and rifampicin, stimulated us to make an attempt for the development of a new class of potent antitubercular agents by modifying the structures of existing drugs. Aiming this, an efficient synthesis of glucose linked-isonicotinoyl-1,3,4-thiadiazolidines has been carried out. Method: The title compounds have been synthesized through cyclocondensation reaction of 1- isonicotinoyl-4-aryl thiosemicarbazides with N-tetra-O-acetyl-β-D-glucopyranosyl isocyanodichloride. The structures of newly synthesized compounds were verified by IR, 1H NMR, 13C NMR, mass spectrometry and elemental analyses. The title compounds were evaluated for their in vitro antitubercular potency against M. tuberculosis H37Rv strain using Lowenstein-Jensen method. Results: A few title compounds were found to be equipotent with the reference drug rifampicin, while moderately potent, when compared with the reference drug isoniazid. These compounds were subjected to molecular docking studies and their results were found to be in agreement with the in vitro studies. Conclusion: We reported simple and efficient protocol for the synthesis of series of bioactive glucoselinked isonicotinoyl-1,3,4-thiadiazolidines by utilizing N-tetra-O-acetyl-β-D-glucopyranosyl isocyanodichloride as a suitable reagent for glycosylation. This approach is a valuable addition to the fastdeveloping field of glucose-linked heterocycles and might be used to develop new potential drugs. We demonstrated the introduction of isonicotinoyl and glucosyl moieties in single molecular framework which may prove beneficial for developing new class of antitubercular agents.

  背景：最近出现了对异烟肼和利福平这两种主要有效药物具有耐药性的结核杆菌耐多药菌株，这促使我们尝试通过改变现有药物的结构来开发一类新的强效抗结核药物。为此，我们进行了葡萄糖连接异烟酰基-1,3,4-噻二唑烷的高效合成。 方法：通过 1-异烟酰基-4-芳基硫代氨基甲酸与 N-四-O-乙酰基-β-D-吡喃葡萄糖基异氰基二氯的环缩合反应合成了标题化合物。 通过红外光谱、1H NMR、13C NMR、质谱和元素分析验证了新合成化合物的结构。采用 Lowenstein-Jensen 方法评估了标题化合物对结核杆菌 H37Rv 株的体外抗结核效力。 结果：发现一些标题化合物与参比药物利福平的效力相当，而与参比药物异烟肼相比，效力适中。对这些化合物进行了分子对接研究，发现其结果与体外研究结果一致。 结论：我们报道了利用 N-四-O-乙酰基-β-D-吡喃葡萄糖基异氰基二氯化物作为糖基化的合适试剂，合成一系列具有生物活性的葡萄糖苷联异烟酰基-1,3,4-噻二唑烷的简单而有效的方法。这种方法是对快速发展的葡萄糖连接杂环领域的宝贵补充，可用于开发新的潜在药物。我们展示了在单一分子框架中引入异烟酰基和葡萄糖基的方法，这可能会被证明有利于开发新型抗结核药物。
• Synthesis and Characterization of<i>N</i>-glucosylated 1,3,4-Thiadiazolidines
  作者：Avinash G. Ulhe、Snehal A. Chavan、Baliram N. Berad

  DOI：10.1080/10426507.2014.938743

  日期：2015.2

  A method is presented for the synthesis of 2-tetra-O-acetyl-beta-d-glucopyran-break;osylimino-5-(aryl)imino-1,3,4-thiadiazolidines by the interaction of substituted aryl thiosemicarbazide with peracetylated glucosyl isocyanodichloride to afford N-glucosylated 5-membered 1,3,4-thiadiazolidines and their alternative synthesis by different route involving the interaction of 4-tetra-O-acetyl-beta-d-glucopyranosyl thiosemicarbazide and aryl imino isocyanodichlorides. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, and mass spectrometric analyses.
• Synthesis and Anticancer Activity of Bis-(<i>N</i>-Glucosylated Triazolothiadiazolyl) Alkanes via Cyclocondensation Reaction Involving C–s and C–n Bond formation
  作者：Snehal A. Chavan、Avinash G. Ulhe、Spruha A. Gharad、Baliram N. Berad

  DOI：10.1080/10426507.2015.1083570

  日期：2015.12.2

  A series of bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl) alkanes have been synthesized and were condensed with N-tetra-O-acetyl--D-glucopyranosyl isocyanodichloride to afford biologically active bis-[6-tetra-O-acetyl--D-glucopyranosylimino-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol-4-yl] alkanes. The structures of the new glucosylated heterocyclic compounds have been established by IR, H-1 NMR, and C-13 NMR spectroscopy, and mass spectrometry analyses. Among the synthesized compounds, a few target compounds were screened for their in vitroanticancer activity against two human cancer cell lines, viz. MCF-7 (Breast) and HEPG2 (Liver).
• HASSEL, T.;MUELLER, H. P.;BOESHAGEN, H.
  作者：HASSEL, T.、MUELLER, H. P.、BOESHAGEN, H.

  DOI：——

  日期：——