7-benzyl-3-ethylxanthine | 139927-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-benzyl-3-ethylxanthine
• 英文别名: 3-ethyl-7-benzyl-xanthine；7-Benzyl-3-ethyl-3,7-dihydro-1H-purine-2,6-dione；7-benzyl-3-ethylpurine-2,6-dione
• CAS: 139927-84-7
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: AECJIAHNTLPXQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  7-benzyl-3-ethylxanthine 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 以633 mg的产率得到3-ethyl-7-benzyl-8-chloro-xanthine
  参考文献：
  名称：

  WO2020120450A5

  摘要：

  公开号：

  WO2020120450A5
• 作为产物：
  描述：

  5,6-diamino-1-ethylpyrimidine-2,4(1H,3H)-dione 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 1.08h， 生成 7-benzyl-3-ethylxanthine
  参考文献：
  名称：

  WO2020120450A5

  摘要：

  公开号：

  WO2020120450A5

文献信息

• Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their
  申请人：Hoechst Aktiengesellschaft

  公开号：US05728686A1

  公开（公告）日：1998-03-17

  Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their use as pharmaceuticals A compound of the formula ##STR1## where R.sup.1 and R.sup.3 are identical or different and at least one of the radicals R.sup.1 and R.sup.3 is a radical of the formula XI ##STR2## in which E is a covalent bond or a (C.sub.1 -C.sub.5)-alkyl, are suitable for the production of pharmaceuticals for the treatment of muscular atrophy, cachexia, muscular dystrophy, sepsis, septic shock, endotoxic shock, systemic inflammation response syndrome, adult respiratory distress syndrome, cerebral malaria, chronic pneumonia, pulmonary sarcoidosis, reperfusion damage, scar formation, inflammation of the bowel and ulcerative colitis, as a result of infections, acquired immune deficiency syndrome, cancer, trauma and other disorders having increased protein loss, peripheral circulatory disorders, disorders having altered leucocyte adhesion, and also disorders which are accompanied by an increased or unregulated tumor necrosis factor production such as rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis and other arthritic disorders.

  烷基黄嘌呤磷酰化合物和烷基黄嘌呤磷酰亚胺氧化物及其作为药物的应用 一种具有以下公式的化合物：##STR1##，其中R.sup.1和R.sup.3相同或不同，且至少一个自由基R.sup.1和R.sup.3是具有以下公式XI的自由基：##STR2##，其中E是共价键或（C.sub.1 -C.sub.5）-烷基，适用于生产用于治疗肌萎缩、恶病质、肌营养不良、败血症、败血性休克、内毒素性休克、系统性炎症反应综合征、成人呼吸窘迫综合征、脑型疟疾、慢性肺炎、肺肉芽肿病、再灌注损伤、疤痕形成、肠炎和溃疡性结肠炎、由于感染、获得性免疫缺陷综合症、癌症、创伤以及其他具有增加蛋白质丢失的疾病、外周循环障碍、具有改变的白细胞粘附的疾病，以及那些伴随有肿瘤坏死因子产生增加或不受控制的疾病，如类风湿性关节炎、强直性脊柱炎、骨关节炎和其他关节疾病。
• Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions
  申请人：——

  公开号：US20020198205A1

  公开（公告）日：2002-12-26

  The present invention relates to substituted xanthines of general formula 1 wherein R 1 to R 4 are defined as in claim 1, the tautomers and the stereoisomers thereof, mixtures thereof, the prodrugs and the salts thereof which have valuable pharmacological properties, particularly an inhibiting effect on the activity of the enzyme dipeptidylpeptidase-IV (DPP-IV).

  本发明涉及一般式1的取代黄嘌呤，其中R1至R4如权利要求1中定义，其互变异构体和立体异构体，其混合物，其前药和其盐，具有有价值的药理特性，特别是对酶二肽基肽酶-IV（DPP-IV）活性的抑制作用。
• Use of theophylline derivatives for the treatment and prophylaxis of states of shock, novel xanthine compounds and processes for their preparation
  申请人：Hoechst Aktiengesellschaft

  公开号：US06214992B1

  公开（公告）日：2001-04-10

  Theophylline derivatives having at least one ether function in the structurally modified methyl radical in the 1-position that are useful in the treatment and prophylaxis of states of shock, new xanthine compounds having this substitution pattern, and processes for their preparation.

  在结构上改变的甲基自由基中至少具有一个醚功能的茶碱衍生物，可用于治疗和预防休克状态，具有这种取代模式的新黄嘌呤化合物，以及它们的制备方法。
• Purines. XLIX. Synthesis and Proton Nuclear Magnetic Resonance Study of 3,7-Dialkylxanthines and 1,3,7-Trialkylxanthines.
  作者：Tozo FUJII、Tohru SAITO、Katsumi TAMURA

  DOI：10.1248/cpb.39.2855

  日期：——

  A general synthetic route to 3, 7-dialkylxanthines (type 9) from 3, 7-dialkyladenines (6) [hence from 3- or 7-alkyladenines (11 or 10)] has been established. The route started with ethoxycarbonylation of 1-alkyl-4-(alkylamino)-1H-imidazole-5-carboxamides (7), readily obtainable from 6 by alkaline hydrolysis, and proceeded through cyclization of the resulting carbamates (8) under alkaline conditions. Alkylation of 9 with alkyl halide in N, N-dimethylformamide in the presence of anhydrous K2CO3 extended the above synthetic route to the 1, 3, 7-trialkylxanthine level (type 14). Hydrogenolytic debenzylation of 3-benzyl-1, 7-dimethylxanthine (16), prepared by following this general synthetic route, furnished paraxanthine (26) in fair yield. Conversion of 26 into 3-(4-hydroxy-3-nitrobenzyl)-1, 7-dimethylxanthine (24), isomeric with the bryozoan purine phidolopin (2), was effected through aralkylation with 4-(methoxymethocy)-3-nitrobenzyl bromide (28) followed by O-deprotection.On the basis of proton nuclear magnetic resonance data for the 3, 7-dialkylxanthines (3 and 9b-i) and 1, 3, 7-trialkylxanthines (5 and 14-22) thus prepared, reliable criteria for distinguishing signals of N-alkyl substituents at various positions are put forward.

  从 3，7-二烷基腺嘌呤（6）[进而从 3 或 7-烷基腺嘌呤（11 或 10）]合成 3，7-二烷基黄嘌呤（9 型）的一般合成路线已经确立。该方法首先是对 1-烷基-4-（烷基氨基）-1H-咪唑-5-羧酰胺（7）进行乙氧基羰基化，通过碱性水解很容易从 6 中得到，然后在碱性条件下对得到的氨基甲酸酯（8）进行环化。在无水 K2CO3 的存在下，9 在 N，N-二甲基甲酰胺中与烷基卤化物发生烷基化反应，将上述合成路线扩展到 1，3，7-三烷基黄嘌呤水平（类型 14）。按照上述一般合成路线制备的 3-苄基-1，7-二甲基黄嘌呤（16）进行氢解去苄基化反应，可以得到副黄嘌呤（26），收率尚可。将 26 转化为 3-（4-羟基-3-硝基苄基）-1,7-二甲基黄嘌呤（24），与红藻嘌呤 phidolopin（2）是同分异构体，通过与 4-（甲氧基甲基）-3-硝基苄基溴（28）酰化，然后进行 O-脱保护。根据由此制备的 3，7-二烷基黄嘌呤（3 和 9b-i）和 1，3，7-三烷基黄嘌呤（5 和 14-22）的质子核磁共振数据，提出了区分不同位置上 N-烷基取代基信号的可靠标准。
• Use of xanthine derivatives for reducing the pathological hyperreactivity of eosinophilic granulocytes, novel xanthine compounds and process for their preparation
  申请人：Hoechst Aktiengesellschaft

  公开号：US20020010333A1

  公开（公告）日：2002-01-24

  Use of xanthine derivatives for reducing the pathological hyperreactivity of eosinophilic granulocytes, novel xanthine compounds and process for their preparation. Tertiary 1-(hydroxyalkyl)-4-alkylxanthines are suitable for the production of pharmaceuticals for the treatment of disorders which is associated with a pathologically increased reactivity of eosinophilic granulocytes. Novel xanthine derivatives and process for their preparation are described.

  黄嘌呤衍生物的使用可降低嗜酸性粒细胞的病理性高反应性，新型黄嘌呤化合物及其制备方法。三级1-(羟基烷基)-4-烷基黄嘌呤适用于生产用于治疗与嗜酸性粒细胞病理性增强反应性相关的疾病的药物。描述了新型黄嘌呤衍生物及其制备方法。