2',3',5'-tri-O-acetyl-2-[3-(4-chlorophenyl)aminocarbonyltriazene-1-yl]adenosine | 527684-68-0

• 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: 2',3',5'-tri-O-acetyl-2-[3-(4-chlorophenyl)aminocarbonyltriazene-1-yl]adenosine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-amino-2-[(E)-[(4-chlorophenyl)carbamoylamino]diazenyl]purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 527684-68-0
• 化学式: C₂₃H₂₄ClN₉O₈
• 分子量: 589.952
• InChiKey: CFYNWIBTNYBJPS-QTQZEZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  224
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-2-[3-(4-chlorophenyl)aminocarbonyltriazene-1-yl]adenosine 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以73%的产率得到2-[3-(4-chlorophenyl)aminocarbonyltriazene-1-yl]adenosine
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j
• 作为产物：
  描述：

  6-Azido-2-nitro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 在 palladium on activated charcoal sodium periodate 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 4.0h， 生成 2',3',5'-tri-O-acetyl-2-[3-(4-chlorophenyl)aminocarbonyltriazene-1-yl]adenosine
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j