Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid) | 15354-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid)
• 英文别名: Methyl-5-S-acetyl-2,3-O-isopropyliden-5-thio-β-D-ribofuranosid；S-[[(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl] ethanethioate
• CAS: 15354-43-5
• 化学式: C₁₁H₁₈O₅S
• 分子量: 262.327
• InChiKey: HHLZURZZYHAHRW-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid) 在 sodium tetrahydroborate 、 硫酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 5-thio-D-ribopyranose
  参考文献：
  名称：

  Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-d-ribopyranosides as well as their 2-deoxy and 2,3-dideoxy derivatives possessing antithrombotic activity

  摘要：

  1,2,3,4-Tetra-O-acetyl-5-thio-D-ribopyranose as well as its 1-bromide were used as donors in the reaction with 4-cyano- and 4-nitrobenzenethiol to give the corresponding thiogrycosides in different anomeric ratios depending on the reaction conditions. Zemplen deacetylation afforded 4-cyanophenyl as well as 4-nitrophenyl 1,5-dithio-alpha- and beta-D-ribopyranosides, respectively. 1,3,4-Tri-O-acetyl-2-deoxy-5-thio-D-erythro-pentopyranose was synthesized from methyl 2-deoxy-D-erythro-pentofuranoside and was coupled with 4-cyano- and 4-nitrobenzenethiol to give anomeric mixtures from which 4-cyanophenyl as well. as 4-nitrophenyl. 1,5-dithio-beta-D-erythro-pentopyranosides were isolated after deacetylation. 1,4-Di-O-acetyl-2,3-dideoxy-5-thio-D-glycero-pentopyranose was obtained starting from 1,2;5,6-di-O-isopropylidene-D-mannitol and used as the donor in the glycosylation reaction with 4-cyano- and 4-nitrobenzenethiol. The resulting anomeric mixtures were separated to give, after deacetylation, 4-cyanophenyl as well as 4-nitrophenyl 2,3-dideoxy-1,5-dithio-beta-D-glycero-pentopyranosides. All of these thioglycosides showed significant antithrombotic activity on rats after oral administration. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00175-5
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid)
  参考文献：
  名称：

  含有衍生自碳水化合物的配体的新型金（I）和金（III）配合物的合成，表征，细胞毒性和抗结核活性。

  摘要：

  合成了含有D-半乳糖，D-核糖和D-葡萄糖基-1,5-内酯衍生物的新型金（I）和金（III）配合物，并通过IR，（1）H和（13）C进行了表征NMR，高分辨率质谱和循环伏安法。体外评估了这些化合物对三种类型的肿瘤细胞的细胞毒性：宫颈癌（HeLa）乳腺腺癌（MCF-7）和胶质母细胞瘤（MO59J），以及一种非肿瘤细胞系：人肺成纤维细胞（GM07492A）。评估它们的抗结核活性，并以μg/ mL的最低抑菌浓度（MIC90）表示。通常，金（I）配合物比金（III）配合物更具活性，例如，金（I）配合物（1）的毒性是金（III）配合物（8）的约8.8倍和细胞毒性的7.6倍。 MO59J和MCF-7电池。核糖和烷基膦衍生物的配合物比半乳糖和芳基膦的配合物更具活性。噻唑烷环的存在不能改善细胞毒性。细胞毒性活性的研究表明，金（I）复合物具有有效的抗肿瘤活性，在所有测试的肿瘤细胞系中比顺铂更具活性。即使与一

  DOI：

  10.1007/s10534-015-9870-8

文献信息

• Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates
  作者：Joana Darc Souza Chaves、Jaqueline Lopes Damasceno、Marcela Cristina Ferreira Paula、Pollyanna Francielli de Oliveira、Gustavo Chevitarese Azevedo、Renato Camargo Matos、Maria Cristina S. Lourenço、Denise Crispim Tavares、Heveline Silva、Ana Paula Soares Fontes、Mauro Vieira de Almeida

  DOI：10.1007/s10534-015-9870-8

  日期：2015.10

  μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (1) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (8) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity

  合成了含有D-半乳糖，D-核糖和D-葡萄糖基-1,5-内酯衍生物的新型金（I）和金（III）配合物，并通过IR，（1）H和（13）C进行了表征NMR，高分辨率质谱和循环伏安法。体外评估了这些化合物对三种类型的肿瘤细胞的细胞毒性：宫颈癌（HeLa）乳腺腺癌（MCF-7）和胶质母细胞瘤（MO59J），以及一种非肿瘤细胞系：人肺成纤维细胞（GM07492A）。评估它们的抗结核活性，并以μg/ mL的最低抑菌浓度（MIC90）表示。通常，金（I）配合物比金（III）配合物更具活性，例如，金（I）配合物（1）的毒性是金（III）配合物（8）的约8.8倍和细胞毒性的7.6倍。 MO59J和MCF-7电池。核糖和烷基膦衍生物的配合物比半乳糖和芳基膦的配合物更具活性。噻唑烷环的存在不能改善细胞毒性。细胞毒性活性的研究表明，金（I）复合物具有有效的抗肿瘤活性，在所有测试的肿瘤细胞系中比顺铂更具活性。即使与一
• Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-d-ribopyranosides as well as their 2-deoxy and 2,3-dideoxy derivatives possessing antithrombotic activity
  作者：Éva Bozó、Sándor Boros、János Kuszmann

  DOI：10.1016/s0008-6215(99)00175-5

  日期：1999.9

  1,2,3,4-Tetra-O-acetyl-5-thio-D-ribopyranose as well as its 1-bromide were used as donors in the reaction with 4-cyano- and 4-nitrobenzenethiol to give the corresponding thiogrycosides in different anomeric ratios depending on the reaction conditions. Zemplen deacetylation afforded 4-cyanophenyl as well as 4-nitrophenyl 1,5-dithio-alpha- and beta-D-ribopyranosides, respectively. 1,3,4-Tri-O-acetyl-2-deoxy-5-thio-D-erythro-pentopyranose was synthesized from methyl 2-deoxy-D-erythro-pentofuranoside and was coupled with 4-cyano- and 4-nitrobenzenethiol to give anomeric mixtures from which 4-cyanophenyl as well. as 4-nitrophenyl. 1,5-dithio-beta-D-erythro-pentopyranosides were isolated after deacetylation. 1,4-Di-O-acetyl-2,3-dideoxy-5-thio-D-glycero-pentopyranose was obtained starting from 1,2;5,6-di-O-isopropylidene-D-mannitol and used as the donor in the glycosylation reaction with 4-cyano- and 4-nitrobenzenethiol. The resulting anomeric mixtures were separated to give, after deacetylation, 4-cyanophenyl as well as 4-nitrophenyl 2,3-dideoxy-1,5-dithio-beta-D-glycero-pentopyranosides. All of these thioglycosides showed significant antithrombotic activity on rats after oral administration. (C) 1999 Elsevier Science Ltd. All rights reserved.