3-苄基-7-氯-3H-[1,2,3]-噻唑并[4,5-d]嘧啶 | 21410-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 中文名称: 3-苄基-7-氯-3H-[1,2,3]-噻唑并[4,5-d]嘧啶
• 中文别名: 3-苄基-7-氯-3H-[1,2,3]-噻唑并[4,5-D]嘧啶
• 英文名称: 7-chloro-3-benzyl-3H-1,2,3-triazolo[4,5-d]pyrimidine
• 英文别名: 3-benzyl-7-chloro-3H-[1,2,3]triazolo[4,5-d]pyrimidine；3-benzyl-7-chloro-1,2,3-triazolo[4,5-d]pyrimidine；3-benzyl-7-chlorotriazolo[4,5-d]pyrimidine
• CAS: 21410-06-0
• 化学式: C₁₁H₈ClN₅
• 分子量: 245.671
• InChiKey: KVYUVZPCMWVWAU-UHFFFAOYSA-N

物化性质

• 沸点：
  454.9±35.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，惰性气体

反应信息

• 作为反应物：
  描述：

  3-苄基-7-氯-3H-[1,2,3]-噻唑并[4,5-d]嘧啶 在 氨 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 8-aza-9-benzyladenine
  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：

  5-氨基-1-苄基-1H-1,2,3-噻唑-4-羧胺 在 氯化亚砜 、 sodium ethanolate 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 3-苄基-7-氯-3H-[1,2,3]-噻唑并[4,5-d]嘧啶
  参考文献：
  名称：

  激动素嘌呤等排体的细胞保护活性

  摘要：

  激动素 ( N 6 -furfuryladenine) 是细胞分裂素家族的一种植物生长物质，已在动物模型中显示可调节衰老和各种与年龄相关的病症。在这里，我们报告了嘌呤环被其他双环杂环取代的激动素等排体的合成，以及它们在体外几种活性的生物学评价与神经退行性疾病相关的模型。我们的研究结果表明激动素等排体保护 Friedreich 共济失调患者来源的成纤维细胞免受谷胱甘肽耗竭，保护神经元样 SH-SY5Y 细胞免受谷氨酸诱导的氧化损伤，并纠正来自家族性自主神经功能障碍患者的成纤维细胞中 ELP1 基因的异常剪接。尽管激动素衍生物的作用机制尚不清楚，但我们的数据表明某些嘌呤等排体的细胞保护活性是由它们减少氧化应激的能力介导的。此外，对人造膜和模型肠道和血脑屏障的渗透研究表明，这些化合物可口服，并可到达中枢神经系统。总体，

  DOI：

  10.1016/j.bmc.2021.115993

文献信息

• Synthesis and Plant Growth Regulating Activity of New Triazolo- and Pyrazolopyrimidine Derivatives Of Aminomethyl, Aminoalkyloxymethyl Dimethylphosphine Oxides and (Aminomethane)Phosphonic Acid Esters
  作者：Elena Stanoeva、Sabi Varbanov、Vera Alexieva、Iskren Sergiev、Vesselina Vasileva、Marieta Rashkova、Angelina Georgieva

  DOI：10.1080/10426500008076331

  日期：2000.2

  Abstract New triazolo[4,5-d]pyrimidine and pyrazolo[3,4-d]pyrimidine derivatives of aminomethyl-and aminomethyloxymethyl dimethylphosphine oxides 8–14 as well as of esters of (aminomethane) phosphonic acid 18–20 were synthesized. The structure of the compounds prepared was confirmed by means of elemend analysis, IR, 1H- and 31P(1H)-NMR spectroscopy. Tertiary phosphine oxides 8, 9 and 12 as well as

  摘要 合成了氨甲基和氨甲氧基甲基二甲基膦氧化物 8-14 以及（氨基甲烷）膦酸酯 18-20 的新三唑并[4,5-d]嘧啶和吡唑并[3,4-d]嘧啶衍生物。制备的化合物的结构通过元素分析、IR、1H-和31P(1H)-NMR光谱证实。叔氧化膦 8、9 和 12 以及膦酸酯 20 显示出除草和植物生长调节活性。
• Compounds containing a N-heteroaryl moiety linked to fused ring moieties for the inhibition of NAD(P)H oxidases and platelet activation
  申请人：Vasopharm Biotech GmbH

  公开号：EP1598354A1

  公开（公告）日：2005-11-23

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sulfur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5-d]pyrimidine-7-yl radical. The invention also relates to a process for the preparation of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  该发明涉及含有N-杂环芳基团的化合物，该化合物通过氧、硫或氮，或通过亚甲基桥和氧、硫或氮连接到融合环基团，特别是到1,2,3-三唑并[4,5-d]嘧啶-7-基自由基。该发明还涉及一种制备所述化合物的方法以及在治疗NAD(P)H氧化酶相关疾病和疾病以及抑制血小板活化的药物中的使用。
• Novel 3-Aralkyl-7-(amino-substituted)-1,2,3-triazolo[4,5-<i>d</i>]pyrimidines with High Affinity toward A₁ Adenosine Receptors
  作者：Laura Betti、Giuliana Biagi、Gino Giannaccini、Irene Giorgi、Oreste Livi、Antonio Lucacchini、Clementina Manera、Valerio Scartoni

  DOI：10.1021/jm9701334

  日期：1998.2.1

  2,3-triazolo[4,5-d]pyrimidine derivatives bearing various amino substituents at the 7 position and one of three lipophilic substituents at the 3 position (benzyl, phenethyl, or 2-chlorobenzyl) were prepared starting from the corresponding 7-chloro compounds, by nucleophilic substitution by the appropriate amine. Radioligand binding assays at bovine brain adenosine A1 and A2A receptors showed that some

  制备三个系列的几种1,2,3-三唑并[4,5-d]嘧啶衍生物，它们在7位带有各种氨基取代基，在3位带有三个亲脂性取代基之一（苄基，苯乙基或2-氯苄基）从相应的7-氯化合物开始，通过适当的胺进行亲核取代。牛脑腺苷A1和A2A受体的放射性配体结合分析表明，某些化合物对A1受体亚型具有很高的亲和力和选择性。特别是生物学结果表明，在7位带有环烷基氨基（环戊基和环己基氨基）或芳烷基氨基（α-甲基苄基和1-甲基-2-苯基乙基氨基或苯丙氨基）取代基的化合物是活性最高的衍生物。在3位的最佳亲脂取代基是2-氯苄基（A1亲和力Ki <50 nM），其次是苄基，然后是苯乙基。这种结构-活性关系（SAR）的模式与先前报道的类似的1,2,3-三唑并吡啶并恶嗪衍生物（Biagi等，1994，1995，1996）相似，只是带有取代芳族胺的化合物具有普遍意义。并大大降低A1受体的亲和力。这些事实使我们能够将这些分子归因于
• 1,2,3-Triazolo[4,5-<i>e</i>]-1,2,4-triazolo[3,4-<i>c</i>]pyrimidines
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Clementina Manera、Valerio Scartoni

  DOI：10.1002/jhet.5570360514

  日期：1999.9

  Some new 1,2,3-triazolo[4,5-e]-1,2,4-triazolo[3,4-c]pyrimidmes were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyrimidines via the formation of the 1,2,4-triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate to give the expected tricyclic derivatives 7, 8 and 9. Intramolecular cyclization of

  一些新的1,2,3-三唑并[4,5- ë ] -1,2,4-三唑并[3，4 - c ^ ] pyrimidmes制备来自相应的1,2,3-三唑并开始并[4,5- d ]嘧啶通过形成1,2,4-三唑环。因此，合适的肼衍生物6用原甲酸三乙酯缩合，原乙酸三乙酯和三乙基orthobenzoate，得到预期三环衍生物7，8和9。乙氧基羰基肼基衍生物10的分子内环化得到在3位带有羟基的三环化合物11。该v在结合测定中针对A 1和A 2A腺苷受体测试了-三唑-三唑并嘧啶衍生物，但它们没有显示任何受体亲和力。
• [EN] COMPOUNDS CONTAINING A N-HETEROARYL MOIETY LINKED TO FUSED RING MOIETIES FOR THE INHIBITION OF NAD(P)H OXIDASES AND PLATELET ACTIVATION<br/>[FR] COMPOSES COMPRENANT UNE FRACTION N-HETEROARYLE LIEE A DES FRACTIONS DE NOYAU FUSIONNEES ET DESTINES A L'INHIBITION DES NAD(P)H OXYDASES ET DE L'ACTIVATION DE PLAQUETTES
  申请人：VASOPHARM BIOTECH GMBH

  公开号：WO2005111041A1

  公开（公告）日：2005-11-24

  The invention relates to compounds containing a N-heteroaryl moiety, which is linked via oxygen, sulfur or nitrogen, or via a methylene bridge and oxygen, sul­fur or nitrogen to a fused ring moiety, in particular to the 1,2,3-triazolo[4,5­d]pyrimidine-7-yl radical. The invention also relates to a process for the prepara­tion of said compounds and the use thereof in drugs for the treatment of NAD(P)H oxidases-related diseases and disorders and inhibition of platelet activation.

  本发明涉及一种含有N-杂芳基基团的化合物，该基团通过氧、硫或氮或通过亚甲基桥和氧、硫或氮连接到融合环基团上，特别是1,2,3-三唑并[4,5-d]嘧啶-7-基自由基。本发明还涉及制备该化合物的方法以及在治疗NAD（P）H氧化酶相关疾病和障碍以及抑制血小板活化的药物中使用该化合物的用途。