3,7-二甲基-8-苯基黄嘌呤 | 149981-18-0

• 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: 3,7-二甲基-8-苯基黄嘌呤
• 英文名称: 3,7-dimethyl-8-phenylxanthine
• 英文别名: 3,7-Dimethyl-8-phenyl-3,7-dihydro-purine-2,6-dione；3,7-dimethyl-8-phenylpurine-2,6-dione
• CAS: 149981-18-0
• 化学式: C₁₃H₁₂N₄O₂
• 分子量: 256.264
• InChiKey: KDTLLXKDFVEQBB-UHFFFAOYSA-N

物化性质

• 密度：
  1.422±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7-二甲基-8-苯基黄嘌呤 在 吡啶 、 sodium hydroxide 、 tetraphosphorus decasulfide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 6-((R)-1-Hydroxymethyl-propylamino)-3,7-dimethyl-8-phenyl-3,7-dihydro-purin-2-one
  参考文献：
  名称：

  咪唑并[2,1-i]嘌呤-5-酮和相关三环水溶性嘌呤衍生物：有效的 A(2A)-和 A(3)-腺苷受体拮抗剂。

  摘要：

  一系列由黄嘌呤衍生物衍生的三环咪唑并[2,1-i]嘌呤酮和扩环类似物已被制备作为腺苷受体（AR）拮抗剂。与黄嘌呤相比，三环化合物由于碱性氮原子在生理条件下可以质子化而表现出更高的水溶性。引入的取代基分别赋予 A(2A) 或 A(3) AR 较高的亲和力。开发了一种新的毛细管电泳方法，使用天然和改性 β-环糊精作为手性鉴别剂来测定选定手性产物的对映体纯度。这些化合物在大鼠脑 A(1) 和 A(2A) AR 的放射性配体结合测定中进行了研究。另外，还对选定的化合物进行了人重组 A(3) AR 的放射性配体结合测定以及大鼠脂肪细胞膜的 A(1) AR、大鼠 PC 12 细胞膜的 A(2A) AR 的功能研究（腺苷酸环化酶测定）、和小鼠 NIH 3T3 细胞膜的 A(2B) AR。结构-活性关系与相应的黄嘌呤衍生物相似。与 8-苯乙烯基黄嘌呤衍生物相比，2-苯乙烯基咪唑嘌呤酮对 A(2A) AR 的效力较低。

  DOI：

  10.1021/jm011093d
• 作为产物：
  描述：

  3,7-Dimethyl-6-methylthio-2-oxopurin 在 dibromobis(triphenylphosphine)nickel(II) 、 四氯苯醌 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 3,7-二甲基-8-苯基黄嘌呤
  参考文献：
  名称：

  Syntheses of 6- or 8-Carbon-Substituted 2-Oxopurines

  摘要：

  3,7-二甲基-6-甲硫基-2-氧嘌呤（1）与格氏试剂或有机锂的反应生成了8-加成物2，而3,7-二甲基-2-氧嘌呤（6）的相应反应则生成了6-加成物7。加成物2和7分别被转化为8-取代的可可碱4和6-取代的3,7-二甲基-2-氧嘌呤8。8-氯可可碱（5）在催化量NiBr2·(PPh3)2存在下与格氏试剂反应，良好产率地生成了4。

  DOI：

  10.1055/s-1994-25439

文献信息

• Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors
  作者：Kenneth A. Jacobson、Dan Shi、Carola Gallo-Rodriguez、Malcolm Manning、Christa Muller、John W. Daly、John L. Neumeyer、Leonidas Kiriasis、Wolfgang Pfleiderer

  DOI：10.1021/jm00070a007

  日期：1993.9

  An aryl p-(trifluoromethyl) substituent increases the affinity of 1,3-disubstituted 8-phenylxanthines at A2a-adenosine receptors, while having little effect on affinity at Al-adenosine receptors. In contrast, an aryl p-(trifluoromethyl) substituent has little effect on affinity of 3,7-disubstituted and 1,3,7-trisubstituted 8-phenylxanthines. An aryl p-sulfo substituent reduces affinity of all 8-phenylxanthines at A1-and A2a-adenosine receptors. An 8-(trifluoromethyl) substituent markedly reduces affinity of 1,3-dialkylxanthines at both A1- and A2a-adenosine receptors. In contrast, 8-(trifluoromethyl)caffeine retains affinity for A2a-adenosine receptors, but does lose affinity for A1-adenosine receptors. 8-Bromo-, 8-acryl-, and 8-pent-1-enylcaffeines are also selective for A2-adenosine receptors, while 8-cyclobutylcaffeine is nonselective. 8-[trans-2-(tert-butyloxycarbonyl)vinylcaffeine is 20-fold selective for Aza vs A1 receptors.
• Synthesis and Structure−Activity Relationships of 3,7-Dimethyl-1-propargylxanthine Derivatives, A_2A-Selective Adenosine Receptor Antagonists
  作者：Christa E. Müller、Uli Geis、Jo Hipp、Ulrike Schobert、Wolfram Frobenius、Maciej Pawłowski、Fumio Suzuki、Jesús Sandoval-Ramírez

  DOI：10.1021/jm970515+

  日期：1997.12.1

  A series of 8-substituted derivatives of 3,7-dimethyl-1-propargylxanthine (DMPX) was synthesized and investigated as A(2A) adenosine receptor antagonists. Different synthetic strategies for the preparation of DMPX derivatives and analogues were explored. A recently developed synthetic procedure starting from 3-propargyl-5,6-diaminouracil proved to be the method of choice for the preparation of this type of xanthine derivatives. The novel compounds were investigated in radioligand binding studies at the high-affinity adenosine receptor subtypes A(1) and A(2A) and compared with standard A(2A) adenosine receptor antagonists. Structure-activity relationships were analyzed in detail. 8-Styryl-substituted DMPX derivatives were identified that exhibit high affinity and selectivity for A(2A) adenosine receptors, including 8-(m-chlorostyryl)-DMPX (CS-DMPX, K-i A(2A) = 13 nM, 100-fold selective), 8-(m-bromostyryl)-DMPX (BS-DMPX, K-i A(2A) = 8 nM, 146-fold selective), and 8-(3,4-dimethoxystyryl)-DMPX (K-i A(2A) = 15 nM, 167-fold selective). These and other novel compounds are superior to the standard A(2A) adenosine receptor antagonists KF17837 (4) and CSC (5) with respect to A(2A) affinity and/or selectivity.
• MATERIALS AND METHODS FOR BINDING NUCLEIC ACIDS TO SURFACES
  申请人：Lyles, Mark B.

  公开号：EP1305328A2

  公开（公告）日：2003-05-02
• [EN] MATERIALS AND METHODS FOR BINDING NUCLEIC ACIDS TO SURFACES<br/>[FR] MATERIELS ET METHODES DE FIXATION D'ACIDES NUCLEIQUES A DES SURFACES
  申请人：LYLES MARK B

  公开号：WO2002008237A2

  公开（公告）日：2002-01-31

  Surfaces contaning high purity silica (silicon dioxide) exhibit high loading potential for nucleic acids. Formulations containing nucleic acids and materials which mask the electrostatic interactions between the nucleic acids and surfaces are disclosed. By masking the phosphate charges of the nucleic acids, undersired interactions may be minimized or eliminated, thereby allowing the covalent boding of the nucleic acids to the surface to proceed. The use of such formulations additionally minimizes nonspecific binding of the nucleic acids to the surface. Examples of materials to be included in such formulations include cations, xanthines, hexoses, purines, arginine, lysine, polyarginine, polylysine, and quaternary ammonium salts.
• Imidazo[2,1-<i>i</i>]purin-5-ones and Related Tricyclic Water-Soluble Purine Derivatives:  Potent A_2A- and A₃-Adenosine Receptor Antagonists
  作者：Christa E. Müller、Mark Thorand、Ramatullah Qurishi、Martina Diekmann、Kenneth A. Jacobson、William L. Padgett、John W. Daly

  DOI：10.1021/jm011093d

  日期：2002.8.1

  most potent compound at A(2A) ARs was (S)-1,4-dimethyl-8-ethyl-2-styryl-imidazo[2,1-i]purinone (S-25) exhibiting a K(i) value of 424 nM at rat A(2A) ARs. The compound was highly selective for A(2A) receptors vs A(1) and A(3) ARs. Selectivity vs A(2B) ARs, however, was low. Among the 1-unsubstituted 2-phenyl-imidazo[2,1-i]purin-5-one derivatives, very potent and highly selective antagonists for human

  一系列由黄嘌呤衍生物衍生的三环咪唑并[2,1-i]嘌呤酮和扩环类似物已被制备作为腺苷受体（AR）拮抗剂。与黄嘌呤相比，三环化合物由于碱性氮原子在生理条件下可以质子化而表现出更高的水溶性。引入的取代基分别赋予 A(2A) 或 A(3) AR 较高的亲和力。开发了一种新的毛细管电泳方法，使用天然和改性 β-环糊精作为手性鉴别剂来测定选定手性产物的对映体纯度。这些化合物在大鼠脑 A(1) 和 A(2A) AR 的放射性配体结合测定中进行了研究。另外，还对选定的化合物进行了人重组 A(3) AR 的放射性配体结合测定以及大鼠脂肪细胞膜的 A(1) AR、大鼠 PC 12 细胞膜的 A(2A) AR 的功能研究（腺苷酸环化酶测定）、和小鼠 NIH 3T3 细胞膜的 A(2B) AR。结构-活性关系与相应的黄嘌呤衍生物相似。与 8-苯乙烯基黄嘌呤衍生物相比，2-苯乙烯基咪唑嘌呤酮对 A(2A) AR 的效力较低。