phenyl 3-azido-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside | 258857-69-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 3-azido-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside
• 英文别名: [(2R,3S,4R)-4-azido-2-methyl-6-phenylsulfanyloxan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 258857-69-1
• 化学式: C₁₈H₂₉N₃O₂SSi
• 分子量: 379.599
• InChiKey: APFLCDXHJLFADT-OZJMSWMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 3-azido-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 13.0h， 生成 2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
  参考文献：
  名称：

  Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

  摘要：

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00820-2
• 作为产物：
  描述：

  methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside 在 咪唑 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.83h， 生成 phenyl 3-azido-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside
  参考文献：
  名称：

  Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

  摘要：

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00820-2

文献信息

• 2-Phenylquinoline-Carbohydrate Hybrids: Molecular Design, Chemical Synthesis, and Evaluation of a New Family of Light-Activatable DNA-Cleaving Agents
  作者：Kazunobu Toshima、Ryusuke Takano、Yutaka Maeda、Masataka Suzuki、Akira Asai、Shuichi Matsumura

  DOI：10.1002/(sici)1521-3773(19991216)38:24<3733::aid-anie3733>3.0.co;2-w

  日期：1999.12.16
• The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline–carbohydrate hybrids
  作者：Kazunobu Toshima、Tomohiro Ozawa、Tomonori Kimura、Shuichi Matsumura

  DOI：10.1016/j.bmcl.2004.03.065

  日期：2004.6

  The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two P-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation. (C) 2004 Elsevier Ltd. All rights reserved.
• Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents
  作者：Kazunobu Toshima、Tomonori Kimura、Ryusuke Takano、Tomohiro Ozawa、Akiko Ariga、Yutaka Shima、Kazuo Umezawa、Shuichi Matsumura

  DOI：10.1016/s0040-4020(03)00820-2

  日期：2003.8

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.