5-氨基-1-(2-氯苄基)-1H-1,2,3-三唑-4-甲酰胺 | 93444-91-8

• 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-氯苄基)-1H-1,2,3-三唑-4-甲酰胺
• 英文名称: 5-amino-1-(2-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide
• 英文别名: 5-amino-1-(2-chlorobenzyl)- 1H-1,2,3-triazole-4-carboxamide；5-amino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide；5-amino-1-[(2-chlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide；5-amino-1-[(2-chlorophenyl)methyl]triazole-4-carboxamide
• CAS: 93444-91-8
• 化学式: C₁₀H₁₀ClN₅O
• 分子量: 251.675
• InChiKey: YNHMYRUNFIQMPN-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C
• 沸点：
  515.9±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-amino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid nitrile	93416-68-3	C10H8ClN5	233.66

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1-(2-chlorobenzyl)-5-pivalamido-1H-1,2,3-triazole-4-carboxamide	1433363-02-0	C15H18ClN5O2	335.793
  ——	5-amino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid nitrile	93416-68-3	C10H8ClN5	233.66
  ——	N-(1-(2-chlorobenzyl)-4-cyano-1H-1,2,3-triazol-5-yl)pivalamide	1433363-04-2	C15H16ClN5O	317.778

反应信息

• 作为反应物：
  描述：

  5-氨基-1-(2-氯苄基)-1H-1,2,3-三唑-4-甲酰胺 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 7-Chloro-3-(2-chloro-benzyl)-5-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine
  参考文献：
  名称：

  2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.04.063
• 作为产物：
  描述：

  2-氯苄溴 在 sodium azide 、 sodium ethanolate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 5-氨基-1-(2-氯苄基)-1H-1,2,3-三唑-4-甲酰胺
  参考文献：
  名称：

  NOVEL [1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES

  摘要：

  该发明涉及一种化合物，其化学式为（I），其中A，R1和R2的定义如描述和索赔中所述。化合物的化学式（I）可用作药物。

  公开号：

  US20130116236A1

文献信息

• Aralkyltriazole compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04789680A1

  公开（公告）日：1988-12-06

  1-phenyl-lower alkyl-1H-1,2,3-triazole compounds of the formula ##STR1## in which Ph represents phenyl substituted by up to and including 3 substituents selected from lower alkyl, halogen and trifluoromethyl, alk represents lower alkylidene, and wherein either R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, amino, N-lower alkylamino, N,N-di-lower alkylamino, N-lower alkanoylamino, carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl or R.sub.1 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R.sub.2 represents hydrogen or lower alkyl, have anti-convulsive properties and can be used as medicaments.

  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。
• [EN] TRIAZOLO[4,5-D]PYRIMIDINES AS AGONISTS OF THE CANNABINOID RECEPTOR 2<br/>[FR] TRIAZOLO[4,5-D]PYRIMIDINES COMME AGONISTES DU RÉCEPTEUR CANNABINOÏDE 2
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016071375A1

  公开（公告）日：2016-05-12

  The invention relates to a compound of formula (I) wherein R1to R4and n are defined as in the description and in the claims. The present invention relates to organic compounds useful for therapy and/or prophylaxis in a mammal, and in particular to compounds that are preferential agonists of the Cannabinoid Receptor 2.

  该发明涉及一种化合物，其化学式为（I），其中R1至R4和n的定义如描述和权利要求中所述。本发明涉及对哺乳动物有益的有机化合物，尤其是对大麻素受体2的优先激动剂。
• 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。
• [EN] NOVEL [1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZOLO[4,5-D]PYRIMIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017220516A1

  公开（公告）日：2017-12-28

  The invention relates to a compound of formula (I) containing at least one diazirenyl. The compound of formula (I) is a type-2 cannabinoid (CB2) receptor modulator and can be used as a medicament.

  该发明涉及一种含有至少一种二氮杂芳基的化合物(I)。化合物(I)是一种类型2大麻素（CB2）受体调节剂，可用作药物。
• [EN] NOVEL TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE TRIAZOLO[4,5-D]PYRIMIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015032769A1

  公开（公告）日：2015-03-12

  The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  该发明涉及一种具有化学式（I）的化合物，其中R1至R4的定义如描述和索赔中所述。化合物的化学式（I）可用作药物。