3'-azido-6'-carba-2',3'-dideoxythymidine | 116183-74-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-azido-6'-carba-2',3'-dideoxythymidine
• 英文别名: (+)-1-<<1R,3S,4S>-3-azido-4--cyclopentenyl>-5-methyl-2,4-<1H,3H>-pyrimidindione；(+)-carbocyclic 3'-deoxy-3'-azidothymidine；carba-3'-azido-2'-deoxythymidine；1-[(1R,3S,4S)-3-azido-4-(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2,4-dione
• CAS: 116183-74-5
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: YOJSVMKUJLZMNI-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-azido-6'-carba-2',3'-dideoxythymidine 生成 1-[(1R,3S,4S)-3-amino-4-(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  SHEALY, Y. FULMER;ODELL, C. ALLEN

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-(1R,2R,4R)-2-<(benzoyloxy)methyl>-4-<(benzyloxy)methyl>cyclopentyl methanesulfonate 在 palladium on activated charcoal 重铬酸吡啶 、 sodium azide 、 硫酸 、 叠氮磷酸二苯酯 、 氨 、 氢气 、 sodium methylate 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.0h， 生成 3'-azido-6'-carba-2',3'-dideoxythymidine
  参考文献：
  名称：

  Synthesis of enantiomerically pure carbocyclic 3′-azido-2′, 3′-dideoxythymidine, a potential anti-aids drug

  摘要：

  DOI：

  10.1016/s0040-4039(00)96716-9

文献信息

• Synthesis and Antiviral Evaluation of Carbocyclic 3′-Azidothymidine (AZT) Analogues and TheircycloSal-Phosphate Triesters
  作者：Olaf R. Ludek、Jan Balzarini、Chris Meier

  DOI：10.1002/ejoc.200500719

  日期：2006.2

  Carbocyclic analogues of the anti-HIV dideoxynucleoside 3′-azido-3′-deoxythymidine AZT (1) were synthesized. Starting from the enantiomerically pure carbocyclic 2′-deoxythymidine 2, four different carbocyclic AZT analogues 2,4–6 were prepared. Moreover, the nucleoside analogues were converted into their membrane-permeable cycloSal-phosphate triesters. All compounds were tested in vitro for their anti-HIV

  合成了抗 HIV 双脱氧核苷 3'-叠氮基-3'-脱氧胸苷 AZT (1) 的碳环类似物。从对映体纯碳环 2'-脱氧胸苷 2 开始，制备了四种不同的碳环 AZT 类似物 2,4-6。此外，核苷类似物被转化为它们的膜渗透性环磷酸三酯。所有化合物都在体外测试了它们在人 T 淋巴细胞中的抗 HIV 活性 (CEM/0)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2'-deoxyribonucleoside analogs derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
  作者：J. Beres、G. Sagi、I. Tomoskozi、L. Gruber、E. Baitz-Gacs、L. Otvos、E. De Clercq

  DOI：10.1021/jm00167a011

  日期：1990.5

  lesser extent, (+)-carbocyclic 2'-deoxyadenosine proved to be effective against HSV-1 [minimum inhibitory concentration (MIC): 0.2 and 2 micrograms/mL, respectively] and HSV-2 (MIC: 2 and 20 micrograms/mL, respectively), but virtually inactive against TK- HSV-1 (MIC: 40 and 100 micrograms/mL, respectively). (+)-Carbathymidine was also active against vaccinia virus (2 micrograms/mL). None of the compounds

  对映体纯的（+）-和（-）-碳环胸苷，（-）-碳环3'-表胸苷，（+）-碳环3'-脱氧-3'-叠氮胸苷，（+）-碳环2,3'从（+）-（）的常见手性库中以立体有择的方式合成了-O-脱水胸苷，（+）-碳环3'-O，6'-亚甲基胸苷和（+）-（6'S）-碳环6'-甲基胸苷（1R，5S）-和（-）-（1S，5R）-2-氧杂双环[3.3.0] oct-6-en-3-one并评估其抗病毒活性。（+）-氨基吡啶和较小程度的（+）-碳环2'-脱氧腺苷被证明对HSV-1有效[最低抑制浓度（MIC）：分别为0.2和2微克/ mL]和HSV-2 （MIC：分别为2和20微克/ mL），但实际上对TK-HSV-1没有活性（MIC：分别为40和100微克/ mL）。（+）-氨基甲酸胸苷对牛痘病毒也有活性（2微克/毫升）。这些化合物均未对HIV或其他RNA病毒的复制产生特定影响。
• Carbocyclic analogs of 5'-amino-5'deoxy- and 3'-amino-3'-deoxythymidines
  作者：Y. Fulmer Shealy、C. Allen O'Dell、William M. Shannon、Gussie Arnett

  DOI：10.1021/jm00154a010

  日期：1986.4

  The carbocyclic analogue of 5'-amino-5'-deoxythymidine was synthesized from the carbocyclic analogue of 2,5'-O-anhydrothymidine acetate. The carbocyclic analogues of 3'-amino-3'-deoxythymidine and of 1-(3'-amino-2',3'-di-deoxylyxofuranosyl)thymine (an all-cis structure) were synthesized from the carbocyclic analogues of 5'-O-trityl-2,3'-O-anhydrothymidine and 5'-O-trityl-3'-O-(methylsulfonyl)thymidine

  5'-氨基-5'-脱氧胸苷的碳环类似物由乙酸2,5'-O-脱水胸苷的碳环类似物合成。由5'的碳环类似物合成3'-氨基-3'-脱氧胸苷和1-（3'-氨基-2'，3'-二-脱氧呋喃呋喃糖基）胸腺嘧啶的碳环类似物（全顺式结构）。 -O-三苯甲基-2,3'-O-脱水胸苷和5'-O-三苯甲基-3'-O-（甲基磺酰基）胸苷。5'-氨基-5'-脱氧胸苷的碳环类似物抑制了在L929（小鼠结缔组织）细胞中复制的1型单纯疱疹病毒的TK +株诱导的细胞致病作用（CPE），但并未抑制Vero细胞中的CPE。相反，全顺3'-叠氮基3'-脱氧胸苷类似物在Vero细胞中显示出适度的CPE抑制作用，
• SYNTHESIS OF CARBOCYCLIC NUCLEOTIDES AS POTENTIAL SUBSTRATES FOR THYMIDYLATE KINASE
  作者：O. R. Ludek、C. Meier

  DOI：10.1081/ncn-200060251

  日期：2005.4.1

  Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.
• BERES, J.;SAGI, GY.;TOMOSKOZI, I.;GRUBER, L.;BAITZ-GACS, E.;OTVOS, L.;CLE+, J. MED. CHEM., 33,(1990) N, C. 1353-1360
  作者：BERES, J.、SAGI, GY.、TOMOSKOZI, I.、GRUBER, L.、BAITZ-GACS, E.、OTVOS, L.、CLE+

  DOI：——

  日期：——