1,2,3,5-tetra-O-acetyl-4-thio-D-ribofuranose | 2495-74-1

• 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: 1,2,3,5-tetra-O-acetyl-4-thio-D-ribofuranose
• 英文别名: [(2R,3S,4R)-3,4,5-triacetyloxythiolan-2-yl]methyl acetate
• CAS: 2495-74-1
• 化学式: C₁₃H₁₈O₈S
• 分子量: 334.347
• InChiKey: BWZCFHIQGLRFLH-PFGBXZAXSA-N

物化性质

• 沸点：
  404.8±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3,5-tetra-O-acetyl-4-thio-D-ribofuranose 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 82.0h， 生成 5-(4-thio-β-D-ribofuranosyl)thiophene-3-carboxamide
  参考文献：
  名称：

  与噻唑林有关的C-硫代核糖核苷的合成，构象分析和生物活性。

  摘要：

  呋喃硫呋喃[5β-D-（4'-硫代呋喃呋喃糖基）呋喃-3-羧酰胺，1]和噻吩硫呋喃[5β-D-（4'-硫代呋喃呋喃糖基）噻吩-3-甲酰胺，2]的合成，两个C-硫代核糖核苷类似物描述了噻唑呋林的衍生物。直接三氟乙酸催化呋喃-3-羧酸乙酯与1-O-乙酰基-2,3,5-三-O-苄基-4-硫代-D-呋喃呋喃糖的C-糖基化反应，得到2-和5-糖基化的区域异构体，作为α和β异头物的混合物。将5-（2,3,5-三-O-苄基）-β-D-（4'-硫代呋喃呋喃糖基）呋喃-3-甲酸乙酯（6beta）脱苄基，然后通过与四氢呋喃反应而转化为相应的酰胺（呋喃硫呋喃）氢氧化铵。噻吩-3-羧酸乙酯与1,2,3的相似C-糖基化 氯化锡催化的5-四-O-乙酰基-4-硫代-D-呋喃呋喃糖得到2-和5-糖基化的区域异构体的异头混合物。用甲醇氨将5-（2,3,5-三-O-乙酰基）-β-D-（4'-硫代呋喃呋喃糖基）噻吩-3-羧酸乙

  DOI：

  10.1021/jm990257b
• 作为产物：
  描述：

  mercury(II) diacetate 、 benzyl 2,3,5-tri-O-benzyl-1,4-dithio-D-ribofuranoside 在 三溴化硼 、 溶剂黄146 作用下， 生成 1,2,3,5-tetra-O-acetyl-4-thio-D-ribofuranose
  参考文献：
  名称：

  某些4'-硫代核苷的合成及生物活性

  摘要：

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。

  DOI：

  10.1080/15257779508012449

文献信息

• Improved and large-scale synthesis of certain glycosyl cyanides. Synthesis of 2,5-anhydro-5-thio-d-allononitrile
  作者：Ganesh D. Kini、Charles R. Petrie、William J. Hennen、N.Kent Dalley、Bruce E. Wilson、Roland K. Robins

  DOI：10.1016/s0008-6215(00)90007-7

  日期：1987.1

  The first synthesis of 2,5-anhydro-5-thio-D-allononitrile starting with L-lyxose, via a trifluoromethanesulfonic ester intermediate, has been accomplished. Methods have been developed to achieve a large-scale synthesis of 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-talo-heptononitrile (5). An improved procedure has been developed to synthesize 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulononitrile (9)

  已经通过三氟甲磺酸酯中间体完成了以L-糖为原料的2,5-脱水5-硫代-D-丙腈的首次合成。已经开发了实现3,4,5,7-四-O-乙酰基-2,6-脱水-D-甘油-D-talo-庚腈的大规模合成方法（5）。已经开发出一种改进的方法来合成2,5-脱水-3,4,6-三-O-苯甲酰基-D-古洛腈（9）。通过X射线晶体学分析证实了5和9，2，5-脱水-3,4,6-三-O-苯甲酰基-D-古洛诺硫酰胺的硫代酰胺衍生物的结构。
• Inhibitory Effects of 9-(4-Thio-.BETA.-D-ribo-pentofuranosyl)guanine on Tumor Growth and Angiogenesis
  作者：Shinji Miura、Kohei Yamada、Fumitaka Kano、Yuichi Yoshimura

  DOI：10.1248/bpb.27.520

  日期：——

  Background: To find a nucleoside with anti-angiogenic activity, we tried to screen an active compound from our nucleoside library. Materials and Methods: The compound inhibiting the growth of human umbilical vein endothelial cell (HUVEC) induced by the conditioned medium of lung carcinoma cell line PC-9 was screened. The antitumor activity of the compound was evaluated against murine sarcoma S-180 implanted onto chick embryo chorioallantoic membrane (CAM). Results: 9-(4-Thio-β-D-ribo-pentofuranosyl)guanine (4′-thioguanosine) was found to be a potent inhibitor of the growth of HUVEC. The growth of S-180 implanted onto CAM was also inhibited by 4′-thioguanosine whereas the in vitro growth of S-180 was not inhibited. The administration of 4′-thioguanosine in mice caused unexpected side effect which suggested neurotoxicity. Conclusions: Antitumor effect of 4′-thioguanosine on S-180 was suggested to be due to inhibition of tumor angiogenesis. Because of toxicity of 4′-thioguanosine in mice, further development of the derivatives which have lower toxicity is required.

  背景：为了找到一种具有抗血管生成活性的核苷，我们试图从我们的核苷库中筛选出一种活性化合物。材料与方法：筛选出抑制肺癌细胞株 PC-9 条件培养基诱导的人脐静脉内皮细胞（HUVEC）生长的化合物。对小鼠肉瘤 S-180 植入小鸡胚胎绒毛膜（CAM）的抗肿瘤活性进行了评估。结果研究发现，9-(4-硫代-β-<小>D-核糖-戊呋喃糖基)鸟嘌呤（4′-硫鸟苷）是一种有效的 HUVEC 生长抑制剂。植入 CAM 的 S-180 的生长也受到 4′-硫鸟苷的抑制，而 S-180 的体外生长不受抑制。在小鼠体内施用 4′-硫鸟苷会产生意想不到的副作用，提示有神经毒性。结论4′-硫鸟苷对 S-180 的抗肿瘤作用可能是由于抑制了肿瘤的血管生成。由于 4′-硫鸟苷对小鼠有毒性，因此需要进一步开发毒性更低的衍生物。
• Structure-Activity Relationships of Tiazofurin Analogs: Synthesis and Computational Studies of 4′-Thio Derivatives of Thiophenfurin and Furanfurin
  作者：P. Franchetti、S. Marchetti、L. Cappellacci、M. Grifantini、B. M. Goldstein、D. Dukhan、J-L. Barascut、J-L. Imbach

  DOI：10.1080/15257779908041538

  日期：1999.4

  The synthesis and computational studies of 5-(4-thio-beta-D-ribofuranosyl)-furan-3-carboxamide (furanthiofurin) and 5-(4-thio-beta-D-ribofuranosyl)thiophene-3-carboxamide (thiophenthiofurin) are reported.
• Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹
  作者：Kamal N. Tiwari、John A. Secrist、John A. Montgomery

  DOI：10.1080/15257779408009484

  日期：1994.9

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.
• US5639873A
  申请人：——

  公开号：US5639873A

  公开（公告）日：1997-06-17