1-乙基-7H-嘌呤-6-酮 | 51559-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1-乙基-7H-嘌呤-6-酮
• 英文名称: 1-ethylhypoxanthine
• 英文别名: N'-Ethyl-hypoxanthin；1-Aethyl-hypoxanthin；1-ethyl-1,7(9)-dihydro-purin-6-one；1-ethyl-7H-purin-6-one
• CAS: 51559-59-2
• 化学式: C₇H₈N₄O
• 分子量: 164.167
• InChiKey: WGFUXYVCRPUUHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  275-276 °C
• 沸点：
  455.3±37.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  1-ethyladenine perchlorate 以3%的产率得到
  参考文献：
  名称：

  FUJII, TOZO;SAITO, TOHRU;HISATA, HIROMI;SHINBO, KOJI, CHEM. AND PHARM. BULL., 38,(1990) N2, C. 3326-3330

  摘要：

  DOI：

文献信息

• Purines. XLVII. Dimroth rearrangement versus hydrolytic deamination of 1-ethyladenine.
  作者：Tozo FUJII、Tohru SAITO、Hiromi HISATA、Koji SHINBO

  DOI：10.1248/cpb.38.3326

  日期：——

  The Dimroth rearrangement of 1-ethyladenine (6) to give N6-ethyladenine (11)(91% yield) was accompanied with unusual hydrolytic deaminations to produce hypoxanthine (8)(2%) and 1-ethylhypoxanthine (14)(2%), when carried out in 0.2N aqueous NaOH at 100°C for 7h. Probable pathways leading to these by-products are discussed on the basis of the results of alkaline hydrolysis of 5-amino-N'-ethylimidazole-4-carboxamidine dihydrochloride (5), which yielded both 5-aminoimidazoli-4-carboxamide (9) and 5-amino-N-ethylimidazole-4-carboxamide (12). For structural identification, 14 was alternatively synthesized from inosine (17) through 1-ethylinosine (16), and 12 was synthesized from 16 through 5-amino-N-ethyl-1-β-D-ribofuranosylimidazole-4-carboxamide (15). Comparison of the reaction rates in the Dimroth rearrangements of 6·HClO4 and 1-ethyl-9-methyladenine perchlorate [1·HClO4 (R1=Et; R2=Me)] in H2O at pH 6.92 and 8.70 (ionic strength 1.0) at 70°C has revealed that nonsubstitution at the 9-position decreases the rearrangement rate by a factor of 4-30 under these conditions.

  1-乙基腺苷（6）的迪莫罗斯重排生成N6-乙基腺苷（11）（91%的产率）过程中，伴随着不寻常的水解脱胺反应，产生了次黄嘌呤（8）（2%）和1-乙基次黄嘌呤（14）（2%）。该反应在0.2N氢氧化钠水溶液中于100°C进行7小时。基于5-氨基-N'-乙基咪唑-4-羧酰胺二盐酸盐（5）的碱性水解结果，讨论了导致这些副产物的可能反应途径，该反应生成了5-氨基咪唑-4-羧酰胺（9）和5-氨基-N-乙基咪唑-4-羧酰胺（12）。为了进行结构鉴定，14也通过肌苷（17）合成，经过1-乙基肌苷（16）合成，12则是通过16进一步合成的，反应中间体为5-氨基-N-乙基-1-β-D-核糖苷咪唑-4-羧酰胺（15）。在pH 6.92和8.70（离子强度1.0）下，于70°C比较了6·HClO4和1-乙基-9-甲基腺苷过氯酸盐[1·HClO4（R1=Et; R2=Me）]的迪莫罗斯重排反应速率，结果表明，在这些条件下，9位上不发生取代反应会使重排速率降低4到30倍。
• Bicyclic pyrimidin-4(3h)-ones and analogues and derivatives thereof which modulate the function of the vanilloid-1-receptor(vr1)
  申请人：Bayliss Tracy

  公开号：US20070135454A1

  公开（公告）日：2007-06-14

  Compounds of formula (I); which are useful as therapeutic compounds, particularly in the treatment of pain and other conditions ameliorated by the modulation of the function of the vanilloid-1 receptor (VR1).

  化合物的公式（I）；这些化合物在治疗疼痛和其他通过调节vanilloid-1受体（VR1）功能改善的情况中尤其有用，可以用作治疗化合物。
• 2,3 Substituted fused bicyclic pyrimidin-4(3H)-ones modulating the function of the vanilliod-1receptor (VR1)
  申请人：Brown Rebecca Elizabeth

  公开号：US20090298856A1

  公开（公告）日：2009-12-03

  The use of a compound of formula (I): for the manufacture of a medicament for the treatment of conditions ameliorated by the modulation of the function of the vanilloid-1 receptor (VR1, also known as TRPV1).

  使用化合物(I)的制剂，用于制造治疗通过调节vanilloid-1受体（VR1，又称TRPV1）功能改善的疾病的药物。
• 2,3-Substituted Fused Pyrimidin -4 (3H)-Ones as VR1 Antagonists
  申请人：Bayliss Tracy

  公开号：US20110152242A1

  公开（公告）日：2011-06-23

  A compound of formula (I), wherein W is formula (1); A is a benzene ring, a fÊve-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms independently chosen from O, N and S, providing that no more than one O or S atom is present, or a six-membered heteroaromatic ring containing 1, 2 or 3 N atoms; n is zero, one, two or three; when n is zero or one, V is CH 2 ; when n is two or three, V is CH 2 , O or NR 5 ; when V is CH2, the bond formed by V and an adjacent carbon ring atom is optionally fused to a phenyl ring, a five-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms independently chosen from O, N and S, providing that no more than one O or S is present, or a six-membered heteroaromatic ring containing 1, 2 or 3 N atoms; the ring being optionally substituted by one or more R 1 groups; and R 7 and R 8 are independently hydrogen, hydroxy, halogen or C 1-4 alkyl; Z is a phenyl ring, a five-membered heteroaromatic ring containing one, two, three or four heteroatoms independently chosen from O, N or S, at most one heteroatom being O or S, or a six-membered heteroaromatic ring containing one, two or three N atoms, optionally substituted by one or more groups chosen from halogen, hydroxy, cyano, nitro, NR 2 R 3 or S(O) r NR 2 R 3 where NR 2 R 3 is as defined above, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloC 1-6 alkyl, C 1-6 alkoxy, haloC 1-6 alkoxy, C 1-6 alkylthio, haloC 1-6 alkylthio, C 3-7 cycloalkyl, hydroxyC 1-6 alkyl, a five-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms independently chosen from O, N and S, providing that no more than one O or S atom is present, or a six-membered heteroaromatic ring containing 1, 2 or 3 N atoms; or a pharmaceutically acceptable salt or N-oxide thereof; pharmaceutical compositions comprising them; the compounds for use in methods of treatment; and use of the compounds for manufacturing medicaments for treating pain as VR1 antagonists, including conditions such as depression, GERD, itch and urinary incontinence.

  化合物的公式为(I)，其中W的公式为(1)；A是苯环、含有1、2或3个杂原子（独立地选择O、N和S），但不超过1个O或S原子的五元杂环芳香环，或含有1、2或3个N原子的六元杂环芳香环；n为零、一、二或三；当n为零或一时，V为CH2；当n为二或三时，V为 、O或NR5；当V为 时，由V和相邻的碳环原子形成的键可选择地与苯环、含有1、2或3个杂原子（独立地选择O、N和S），但不超过1个O或S的五元杂环芳香环，或含有1、2或3个N原子的六元杂环芳香环融合；该环可选择地被一个或多个R1基取代；R7和R8独立地为氢、羟基、卤素或C1-4烷基；Z为苯环、含有1、2、3或4个杂原子（独立地选择O、N或S，最多一个杂原子为O或S）的五元杂环芳香环，或含有1、2或3个N原子的六元杂环芳香环，可选择地被一个或多个从卤素、羟基、氰基、硝基、NR2R3或S(O)rNR2R3（其中NR2R3如上所定义）、C1-6烷基、C2-6烯基、C2-6炔基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷基硫基、卤代C1-6烷基硫基、C3-7环烷基、羟基C1-6烷基、含有1、2或3个杂原子（独立地选择O、N和S），但不超过1个O或S原子的五元杂环芳香环，或含有1、2或3个N原子的六元杂环芳香环取代的基团选择地取代；或其药学上可接受的盐或N-氧化物；包含它们的制药组合物；该化合物用于治疗的方法；以及将该化合物用于制造用于治疗疼痛的药物，作为VR1拮抗剂，包括抑郁症、GERD、瘙痒和尿失禁等情况。