CAS: 574-25-4; (2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-Mercapto-9H-Purin-9-yl)Tetrahydrofuran-3,4-Diol

该化合物是纯核素的类似物,其特点是在异氨基分子的6个位置上存在硫磺原子,其化学配方为C10H12N4O5S,并配有与改良的纯碱基相连的糖,该化合物因其潜在的生物活动而引人注目,特别是在抗病毒和抗癌症研究方面,因为它可能干扰核酸新陈代谢. 6-硫诺辛在水中和核素典型的外表特性中溶解,例如由于其盐基和氨基组,能够参与氢结合的能力.硫酸组的存在可以增强稳定性,改变其与丁基化合物(Inosine)的酶和受体的相互作用.因此,6-硫诺因潜在的治疗用途和在研究核糖代谢新化学学方面的作用而对医药化学和生物化学学感兴趣.

英文名称(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-Mercapto-9H-Purin-9-yl)Tetrahydrofuran-3,4-Diol
中文名称6-疏基嘌呤核苷
IUPAC名称(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-mercapto-9H-purin-9-yl)tetrahydrofuran-3,4-diol
其它别名Mercaptopurine-9-D-Riboside, 6-; 6H-Purine-6-Thione, 1,9-Dihydro-9-Beta-D-Ribofuranosyl-; 6-Mercaptoinosine; 6-Mpr; 6-Mp-Riboside; 6-Thiopurine Ribonucleoside; 6-Thiopurine Riboside; 9H-Purine-6-Thiol, 9-β-D-Ribofuranosyl- (6Ci)
CAS编号574-25-4
MFCD编号:MFCD00005743
EINECS号:209-371-5
分子式:C10H12N4O4S分子量:284.29
产品CID: 2506518
产品分类生物化工 → 核苷类药物 → 核苷中间体

相似结构搜索
InChIKey: OJUVLZDWUQUPBF-MGUDNFKCSA-N
InChI=1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7-,10-/m1/s1
计算化学: 氢键受体数6.0氢键供体数4.0可旋转键数2.0

物理性质

熔点220-223 °C(文献)
沸点714.7 °C at 760mmHg
闪点386 °C
密度2.02g/cm3
pKa:8.40±0.20(预测)
PSA:148.51
LogP:-0.8996
折射率1.6270 (estimate)
蒸汽压1.99E-17 mmHg at 25 °C
溶解性Aqueous Base (Slightly), DMSO (Slightly), Methanol (Very Slightly, Heated)
敏感性Store in Cool Dry Place
外观形态白色至米色固体
储存条件请置于阴暗处, 惰性气氛中,冷冻保存, 低于 -20°C
产品应用该化合物是含有抗排生物活性纯净抗异同物;它减少了PPARGT,C/EBPATAL及其目标基因LPL,CD36,AP2和LXRΑ的氨RNA水平.

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

📜2',3',5'-三乙酰肌苷置于4-二甲氨基吡啶,氨,三氯氧磷体系中,用甲醇,乙醇作为反应溶剂,化学反应 20.34H,反应生成 6-疏基嘌呤核苷
参考文献:α,β-Methylene-Adp (Aopcp) Derivatives And Analogues: Development Of Potent And Selective Ecto-5'-Nucleotidase (Cd73) Inhibitors
标题:α,β-Methylene-Adp (Aopcp) Derivatives And Analogues: Development Of Potent And Selective Ecto-5'-Nucleotidase (Cd73) Inhibitors
摘要:Ecto-5'-Nucleotidase (En,Cd73) Catalyzes The Hydrolysis Of Extracellular Amp To Adenosine. En Inhibitors Have Potential For Use As Cancer Therapeutics. The En Inhibitor Alpha,Beta-Methylene-Adp (Aopcp,Adenosine-5'-O-[(Phosphonomethyl)Phosphonic Acid]) Was Used As A Lead Structure,And Derivatives Modified In Various Positions Were Prepared. Products Were Tested At Rat Recombinant En. 6-(Ar)Alkylamino Substitution Led To The Largest Improvement In Potency. N-6-Monosubstitution Was Superior To Symmetrical N-6,N-6-Disubstitution. The Most Potent Inhibitors Were N-6-(4Chlorobenzyl)-(10L,Psb-12441,K-I 7.23 N.M),N-6-Phenylethyl(10H,Psb-12425,K-I 8.04 Nm),And N-6-Benzyl-Adenosine-5'-O[(Phosphonomethyl)Phosphonic Acid] (10G,Psb-12379,K-I 9.03 Nm). Replacement Of The 6-Nh Group In 10G By 0 (10Q,Psb-12431) Or S (10R,Psb-12553) Yielded Equally Potent Inhibitors (10Q,9.20 Nm; 10R,9.50 Am). Selected Compounds Investigated At The Human Enzyme Did Not Show Species Differences; They Displayed High Selectivity Versus Other Ecto-Nudeotidases And Adp-Activated P2Y Receptors. Moreover,High Metabolic Stability Was Observed. These Compounds Represent The Most Potent En Inhibitors Described To Date.
DOI:10.1021/acs.Jmedchem.5B00802