5-氨基-1-(2-氟苄基)-1H-1,2,3-三唑-4-甲酰胺 | 93416-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 5-氨基-1-(2-氟苄基)-1H-1,2,3-三唑-4-甲酰胺
• 英文名称: 5-amino-1-(2-fluorobenzyl)-1H-1,2,3-triazole-4-carboxamide
• 英文别名: 5-amino-1-(o-fluorobenzyl)-1H-1,2,3-triazole-4-carboxamide；5-amino-1-[(2-fluorophenyl)methyl]triazole-4-carboxamide
• CAS: 93416-62-7
• 化学式: C₁₀H₁₀FN₅O
• 分子量: 235.221
• InChiKey: KMIYWNHMQLBIOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氨基-1-(2-氟苄基)-1H-1,2,3-三唑-4-甲酰胺 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 3-(2-fluorobenzyl)-7-chloro-1,2,3-triazolo[4,5-d]pyrimidine
  参考文献：
  名称：

  New amino derivatives of 1,2,3-triazolo[4,5-d]pyrimidines and their affinity towards A1 and A2A adenosine receptors

  摘要：

  Starting from the appropriate azides (4-chlorobenzyl-, 2-thiophenemethyl-, 2-fluorobenzyl-, and 4-fluorobenzylazide in which the variation of the substituent is at the basis of the four series of derivatives (a-d), the 7-aminosubstituted 1,2,3-triazolo[4,5-d]pyrimidines 4 were prepared by a well known synthetic route. The biological activity of compounds 4 was expected on the basis of the presence of particular substituents on N(7), and these substituents were introduced by the reaction of the 7 lactamic carbonyl function, present on precursors 3, with cycloalkyl-, aralkyl- and arylamines. Radioligand binding assays at bovine brain adenosine A(1) and A(2A) receptors showed that some compounds possessed a high affinity and selectivity for the A(1) receptor subtype. Furthermore, biological results indicated that the p-chlorobenzyl substituent lowered receptor binding, compared with the previously prepared benzyl and 2-chlorobenzyl derivatives, suggesting certain particular steric requirements of the lipophilic region which interacts with the benzyl substituent. The thiophenemethyl substituent conferred more activity than the benzyl one. The presence of a fluorine atom on the benzyl group determined a high affinity, especially when it was in the ortho position. Compounds 4c.1 (R = 2-fluorobenzyl, R' = cyclopentyl, Ki = 10.5 nM), 4c.2 (R = 2-fluorobenzyl, R' = cyclohexyl, Ki = 19.5 nM) and 4d.1 (R = 4-fluorobenzyl, R' = cyclopentyl, Ki = 26 nM) were the most active for A(1) receptors. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00205-6
• 作为产物：
  描述：

  1-(叠氮甲基)-2-氟苯 生成 5-氨基-1-(2-氟苄基)-1H-1,2,3-三唑-4-甲酰胺
  参考文献：
  名称：

  Aralkyltriazole compounds

  摘要：

  1-苯基-低级烷基-1H-1,2,3-三唑化合物，其分子式为##STR1##，其中Ph代表苯基，苯基可被低级烷基、卤素和三氟甲基中的一种或多种取代基取代，alk代表低级烷基亚基，且R.sub.1代表氢、低级烷基、低级烷氧基、氨基、N-低级烷基氨基、N,N-二低级烷基氨基、N-低级烷氧酰氨基、碳酰胺、N-低级烷氧酰碳酰胺、N-低级烷基碳酰胺或N,N-二低级烷基碳酰胺，而R.sub.2代表碳酰胺、N-低级烷氧酰碳酰胺、N-低级烷基碳酰胺或N,N-二低级烷基碳酰胺，或者R.sub.1代表碳酰胺、N-低级烷氧酰碳酰胺、N-低级烷基碳酰胺或N,N-二低级烷基碳酰胺，而R.sub.2代表氢或低级烷基，这些化合物具有抗惊厥性质，可用作药物。

  公开号：

  US04789680A1

文献信息

• 3-benzyl-3H-1,2,3-triazolo[4,5-d]pyrimidines, compositions thereof, and
  申请人：Ciba-Geigy Corporation

  公开号：US05204353A1

  公开（公告）日：1993-04-20

  Tbe invention relates to 3H-1,2,3-triazolo[4,5-d]pyrimidine derivatives, especially substituted 3-benzyl-3H-1,2,3-triazolo[4,5-d]-pyrimidines of the general formula ##STR1## in which Ph represents a phenyl radical substituted by halogen, lower alkyl, trifluoromethyl and/or by cyano, R.sub.1 represents a free amino group or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, and R.sub.2 represents hydrogen, lower alkyl, a free amino group, or an amino group that is substituted aliphatically, cycloaliphaically, cycloaliphatically-aliphatically and/or by acyl, in free form or in form of a salt, with the proviso, that in a compound of formula I in free form, wherein R.sub.1 represents N,N-di-C.sub.1 -C.sub.6 -alkylamino in which the two N-C.sub.1 -C.sub.6 -alkyl groups may be the same or different, N-mono-C.sub.1 -C.sub.6 -alkylamino or amino, R.sub.2 is other than hydrogen and other than C.sub.1 - C.sub.6 -alkyl, if Ph represents a phenyl radical which is monosubstituted by halogen or by trifluoromethyl, and to compounds of formula I in free form wherein either Ph is o-fluorophenyl, R.sub.1 is N-mono-methylamino or amino, and R.sub.2 is hydrogen or methyl or wherein Ph is o-fluorophenyl, o-chlorophenyl or m-trifluoromethylphenyl, R.sub.1 is N,N-di-methylamino, and R.sub.2 is hydrogen or wherein Ph is m-fluorophenyl, p-fluorophenyl, o-chlorophenyl, o-trifluoromehylphenyl, m-trifluoromethylphenyl or p-trifluoromethylphenyl, R.sub.1 is N-mono-methylamino, and R.sub.2 is hydrogen. These compounds and salts can be used as pharmaceutical active ingredients and can be produced in a manner known per se.

  该发明涉及3H-1,2,3-三氮唑[4,5-d]嘧啶衍生物，特别是一般式##STR1##的取代3-苄基-3H-1,2,3-三氮唑[4,5-d]-嘧啶化合物，其中Ph代表被卤素、较低烷基、三氟甲基和/或氰基取代的苯基基团，R.sub.1代表自由氨基或被脂肪基、环脂肪基、环脂肪基-脂肪基和/或酰基取代的氨基，R.sub.2代表氢、较低烷基、自由氨基或被脂肪基、环脂肪基、环脂肪基-脂肪基和/或酰基取代的氨基，以自由形式或盐形式存在，但在式I的自由形式化合物中，如果R.sub.1代表N,N-二-C.sub.1-C.sub.6-烷基氨基，其中两个N-C.sub.1-C.sub.6-烷基基团可以相同也可以不同，N-单-C.sub.1-C.sub.6-烷基氨基或氨基，R.sub.2不是氢且不是C.sub.1-C.sub.6-烷基，如果Ph代表被卤素或三氟甲基单取代的苯基基团，以及在自由形式的式I化合物中，其中Ph是o-氟苯基，R.sub.1是N-单-甲基氨基或氨基，R.sub.2是氢或甲基，或者Ph是o-氟苯基、o-氯苯基或m-三氟甲基苯基，R.sub.1是N,N-二-甲基氨基，R.sub.2是氢，或者Ph是m-氟苯基、p-氟苯基、o-氯苯基、o-三氟甲基苯基、m-三氟甲基苯基或p-三氟甲基苯基，R.sub.1是N-单-甲基氨基，R.sub.2是氢。这些化合物和盐可用作药用活性成分，并可按已知方法制备。
• Aralkyltriazolverbindungen
  申请人：CIBA-GEIGY AG

  公开号：EP0114347A2

  公开（公告）日：1984-08-01

  1-Phenylniederalkyl-1H-1,2,3-triazolverbindungen der Formel worin Ph durch Niederalkyl, Halogen und/oder Trifluormethyl substituiertes Phenyl bedeutet, alk Niederalkyliden darstellt, R1 Wasserstoff, Niederalkyl, Niederalkoxy oder eine unsubstituierte oder durch Acyl, Niederalkyl oder Niederalkylen bzw. Aza-, Oxa- oder Thianiederalkylen substituierte Amino- oder Carbamylgruppe bedeutet und R2 für eine unsubstituierte oder durch Acyl, Niederalkyl, Niederalkylen bzw. Aza-, Oxa- oder Thianiederalkylen substituierte Carbamylgruppe oder sofern R1 eine unsubstituierte oder durch Acyl, Niederalkyl oder Niederalkylen bzw. Aza-, Oxa- oder Thianiederalkylen substituierte Aminogruppe darstellt, für Cyano bzw., sofern R, eine unsubstituierte oder durch Acyl, Niederalkyl oder Niederalkylan bzw. Aza-, Oxa- oder Thianiederalkylen substituierte Carbamylgruppe bedeutet, für Wasserstoff oder Niederalkyl steht haben antikonvulsive Eigenschaften und sind als Arzneimittel verwendbar.

  式中的 1-苯基-低级烷基-1H-1,2,3-三唑化合物 其中 Ph 代表被低级烷基、卤素和/或三氟甲基取代的苯基，alk 代表低级亚烷基，R1 代表氢、低级烷基、低级烷氧基或未被取代或被酰基、低级烷基或低级亚烷基取代的氨基或羰基，或R1代表氢、低级烷基、低级烷氧基或未被酰基、低级烷基或低级亚烷基取代或被酰 基、低级烷基或低级亚烷基或氮杂、氧杂或噻二烷基取代的氨基或羰基，或如果 R1 代表未被酰基、低级烷基或低级亚烷基或氮杂、氧杂或噻二烷基取代或被其取代的氨基，则 R2 代表氰基 或其中 R 是未取代的或被酰基、低级烷基或低级亚烷基或氮杂、氧杂或噻二烷基取代的氨基，是氢或低级烷基，具有抗惊厥特性，可用作药物。
• 3H-1,2,3-Triazolo[4,5-d]pyrimidine
  申请人：CIBA-GEIGY AG

  公开号：EP0288431A1

  公开（公告）日：1988-10-26

  Die Erfindung betrifft neue 3H-1,2,3-Triazolo[4,5-d]pyrimidin­derivate, insbesondere substituierte 3-Benzyl-3H-1,2,3-triazolo­[4,5-d]pyrimidine der allgemeinen Formel worin Ph einen durch Halogen, Niederalkyl, Trifluormethyl und/oder Cyano substituierten Phenylrest bedeutet, R₁ eine freie oder aliphatisch, cycloaliphatisch, cycloaliphatisch-aliphatisch und/oder durch Acyl substituierte Aminogruppe darstellt und R₂ für Wasser­stoff, Niederalkyl oder eine freie oder aliphatisch, cycloaliph­tisch, cycloaliphatisch-aliphatisch und/oder durch Acyl substituier­te Aminogruppe steht, und ihre Salze. Diese Verbindungen können als pharmazeutische Wirkstoffe verwendet werden und sind in an sich bekannter Weise herstellbar.

  本发明涉及新的 3H-1,2,3-三唑并[4,5-d]嘧啶衍生物，特别是通式为取代的 3-苄基-3H-1,2,3-三唑并[4,5-d]嘧啶。 其中 Ph 是被卤素、低级烷基、三氟甲基和/或氰基取代的苯基，R₁ 是游离或脂肪族、环脂族、环脂-脂肪族和/或酰基取代的氨基，R₂ 是氢、低级烷基或游离或脂肪族、环脂族、环脂-脂肪族和/或酰基取代的氨基，以及它们的盐。这些化合物可用作活性药物成分，并可用已知的方法制备。
• 2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies
  作者：Giuliana Biagi、Anna Maria Bianucci、Alessio Coi、Barbara Costa、Laura Fabbrini、Irene Giorgi、Oreste Livi、Iolanda Micco、Federica Pacchini、Edoardo Santini、Michele Leonardi、Fatena Ahmad Nofal、Oreste LeRoy Salerni、Valerio Scartoni

  DOI：10.1016/j.bmc.2005.04.063

  日期：2005.8

  A number of N-6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8-azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A(1) ligands, by only three or two steps, are described. At first we prepared a series of 2-phenyl-9-benzyl-8-azaadenines having as N-6 substituent a variously substituted N-phenylcarbamoyl group. Some of these derivatives demonstrated good affinity towards the A(3) subtype but low selectivity. Compounds having p-CF3, p-F and p-OCH3, as substituents on the phenylcarbamoyl group were selected as lead compounds for the second part of this study. Without modifying the N-6 substituent, which would assure A(3) affinity, we varied the 9 and 2 positions on these molecules to enhance selectivity. Some compounds having a p-methyl group on the 2-phenyl substituent showed a very good affinity and selectivity for the A(3) subtype, revealing the first class of A(3) adenosine receptor selective antagonists with a bicyclic structure strictly correlated to the adenine nucleus. The molecular modelling work, carried out using the DOCK program, supplied two models which may be useful for a better understanding of the binding modes. Both models highlighted the preferred interacting tautomeric forms of the antagonists for human A(1) and A(3) receptors. (c) 2005 Elsevier Ltd. All rights reserved.
• US4789680A
  申请人：——

  公开号：US4789680A

  公开（公告）日：1988-12-06