CVT 3003 | 56720-72-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: CVT 3003
• 英文别名: 2-thiophen-2-yl-adenosine；2-Thiophenyl-adenosin；(2R,3R,4S,5R)-2-(6-amino-2-thiophen-2-ylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 56720-72-0
• 化学式: C₁₄H₁₅N₅O₄S
• 分子量: 349.37
• InChiKey: SXXBOJVPHNFPQH-GUSNPEKLSA-N

物化性质

• 沸点：
  620.4±65.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(Thien-2-yl)-6-chloro-9β-(2,3,5-tri-O-acetyl-D-ribofuranosyl)purine 在 氨 作用下， 以 甲醇 为溶剂， 生成 CVT 3003
  参考文献：
  名称：

  腺苷的2取代pi系统衍生物，是通过A2A腺苷受体起作用的冠状血管舒张剂。

  摘要：

  化合物20（CVT-3146--2-[（（N-1-（4-N-甲基羧酰胺基吡唑基）]腺苷衍生物））和化合物31（CVT-3033--A2-[（4-（1-N-戊基吡唑基）腺苷衍生物）]腺苷衍生物）被发现是短效的功能选择性冠状动脉血管扩张剂（CV t0.5分别为5.2 +/- 0.2和3.4 +/- 0.5分钟-大鼠离体心脏50％逆转时间），具有良好的效能（ EC50S = 6.4 +/- 1.2 nM和67.9 +/- 16.7 nM），但是它们对ADO A2A受体的亲和力低（Ki分别为1122 +/- 323 nM和2138 +/- 952 nM;猪纹状体） ）。

  DOI：

  10.1081/ncn-100002306

文献信息

• Synthesis and coronary vasodilating activity of 2-substituted adenosines.
  作者：RYUJI MARUMOTO、YOSHIO YOSHIOKA、OSAMU MIYASHITA、SHUNSUKE SHIMA、KINICHI IMAI、KATSUYOSHI KAWAZOE、MIKIO HONJO

  DOI：10.1248/cpb.23.759

  日期：——

  A large scale preparation of 2-haloadenosines (1) was attained by acetylation of 2-haloinosines (3), followed by chlorination and amination. 2-Alkoxyadenosines (5) were prepared in fairly good yields by protection of both 2'- and 3'-hydroxyl groups of 2-chloroadenosine (1a) or 2-chloroinosine (3a), followed by substitution of the chlorine atom with alkoxy group. In the reaction of 1a with sodium alkoxide, there were obtained some oligomers of 5, of which the structures were elucidated. The reaction of 5-amino-4-cyano-1-β-D-ribofuranosylimidazole with carbon disulfide afforded 2, 6-di-mercapto-9-β-D-ribofuranosylpurine (15), which was converted to 2-mercaptoadenosine (14e) and its S-substituted derivatives. 2-Phenylaminoadenosine (29e) was prepared with comparative ease via 2-phenylamino-2', 3', 5'-tri-O-acetylinosine (32), the synthesis of which was effected by acetylation of 2-phenylaminoinosine (30) with acetylchloride in acetic acid. Many 2-substituted adenosines including O-substituted 2-hydroxyadenosines, S-substituted 2-mercaptoadenosines, N2-substituted 2-aminoadenosines, 2-alkyl- and -aryl-adenosines were prepared, among which several compounds were found to have a remarkable coronary vasodilating potency. Compound (29e) showed not only a strong potency, but also a longer duration of the effect than that of 1a. The structure-coronary vasodilating activity relationship was also discussed.

  通过乙酰化2-卤代次黄嘌呤核苷(3)继以氯化和胺化,制得了2-卤代腺嘌呤核苷(1)的大量样品。通过保护2-氯腺嘌呤核苷(la)或2-氯代次黄嘌呤核苷(3a)的2'-和3'-羟基,然后用烷氧基团取代氯原子,制得了收率相当不错的2-烷氧基腺嘌呤核苷(5)。la与烷醇钠反应,得到5的一些寡聚体,其结构已得到阐明。5-氨基-4-氰基-1-β-D-呋喃核糖基咪唑与二硫化碳反应,生成2,6-二巯基-9-β-D-呋喃核糖基嘌呤(15),可转化为2-巯基腺嘌呤核苷(14e)及其S-取代衍生物。2-苯胺基腺嘌呤核苷(29e)通过2-苯胺基-2',3',5'-三-O-乙酰次黄嘌呤核苷(32)比较容易地制得,而32是通过2-苯胺基次黄嘌呤核苷(30)在乙酸中与乙酰氯反应进行乙酰化来合成的。制备了许多2-取代腺嘌呤核苷,包括O-取代2-羟基腺嘌呤核苷、S-取代2-巯基腺嘌呤核苷、N2-取代2-氨基腺嘌呤核苷、2-烷基和芳基腺嘌呤核苷,其中发现几种化合物具有显著的冠状血管舒张活性。化合物(29e)不仅显示了强大的活性,而且其效果的持续时间比la更长。还讨论了结构-冠状血管舒张活性关系。