6-氯-9-甲基-9H-嘌呤-2-胺 | 3035-73-2

• 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: 6-氯-9-甲基-9H-嘌呤-2-胺
• 英文名称: 2-amino-6-chloro-9-methyl-9H-purine
• 英文别名: 6-chloro-9-methyl-9H-2-purinylamine；6-chloro-9-methyl-9H-purin-2-amine；2-amino-6-chloro-9-methylpurine；6-chloro-9-methyl-purin-2-amine；6-chloro-9-methyl-9H-purin-2-ylamine；2-Amino-6-chlor-9-methyl-purin；6-chloro-9-methylpurin-2-amine
• CAS: 3035-73-2
• 化学式: C₆H₆ClN₅
• mdl: MFCD13192540
• 分子量: 183.6
• InChiKey: DVBOWBHHDZWSOC-UHFFFAOYSA-N

物化性质

• 沸点：
  455.1±55.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-氯-9-甲基-9H-嘌呤-2-胺 在 copper(l) iodide 、 二碘甲烷 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以59%的产率得到6-chloro-2-iodo-9-methyl-9H-purine
  参考文献：
  名称：

  2-Alkynyl-8-aryl-9-methyladenines as Novel Adenosine Receptor Antagonists:  Their Synthesis and Structure−Activity Relationships toward Hepatic Glucose Production Induced via Agonism of the A_2B Receptor

  摘要：

  Novel adenosine antagonists, 2-alkynyl-8-aryl-9-methyladenine derivatives, were synthesized as candidate hypoglycemic agents. These analogues were evaluated for inhibitory activity on N-ethylcarboxamidoadenosine (NECA)-induced glucose production in primary cultured rat hepatocytes. In general, aromatic moieties at the 8-position and alkynyl groups at the 8-position had significantly increased activity compared to unsubstituted compounds. The preferred substituents at the 8-position of adenine were the 2-furyl and 3-fluorophenyl groups. In modifying the alkynyl side chain, change of the ring size, cleavage of the ring, and removal of the hydroxyl group were well tolerated. The order of the stimulatory effects of adenosine agonists on rat hepatocytes was NECA > CPA > CGS21680, which is consistent with involvement of the A(2B) receptor. In Chinese hamster ovary cells stably transfected with human A(2B) receptor cDNA, one of the compounds potent in hepatocytes, 15o (IC50 = 0.42 muM), antagonized NECA-induced stimulation of cyclic AMP production (IC50 = 0.063 muM). This inhibitory effect was much more potent than those of FK453, KF17837, and L249313 which have been reported to be respectively A(1), A(2A), and A(3) selective antagonists. These findings agree very well with the result that, compared to 15o, these selective antagonists for each receptor subtype showed only marginal effects in rat hepatocytes. These results suggest that adenosine agonist-induced glucose production in rat hepatocytes is mediated through the A(2B) receptor. Furthermore, 15o showed hypoglycemic activity in an animal model of noninsulin-dependent diabetes mellitus, the KK-A(y) mice. It is possible that inhibition of hepatic glucose production via the A(2B) receptor could be at least one of the mechanisms by which 15o exerts its in, vivo effects. Further elaboration of this group of compounds may afford novel antidiabetic agents.

  DOI：

  10.1021/jm990499b
• 作为产物：
  描述：

  N1-[5-amino-4-chloro-6-(methylamino)-2-pyrimidinyl]acetamide 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 6-氯-9-甲基-9H-嘌呤-2-胺
  参考文献：
  名称：

  2-Alkynyl-8-aryl-9-methyladenines as Novel Adenosine Receptor Antagonists:  Their Synthesis and Structure−Activity Relationships toward Hepatic Glucose Production Induced via Agonism of the A_2B Receptor

  摘要：

  Novel adenosine antagonists, 2-alkynyl-8-aryl-9-methyladenine derivatives, were synthesized as candidate hypoglycemic agents. These analogues were evaluated for inhibitory activity on N-ethylcarboxamidoadenosine (NECA)-induced glucose production in primary cultured rat hepatocytes. In general, aromatic moieties at the 8-position and alkynyl groups at the 8-position had significantly increased activity compared to unsubstituted compounds. The preferred substituents at the 8-position of adenine were the 2-furyl and 3-fluorophenyl groups. In modifying the alkynyl side chain, change of the ring size, cleavage of the ring, and removal of the hydroxyl group were well tolerated. The order of the stimulatory effects of adenosine agonists on rat hepatocytes was NECA > CPA > CGS21680, which is consistent with involvement of the A(2B) receptor. In Chinese hamster ovary cells stably transfected with human A(2B) receptor cDNA, one of the compounds potent in hepatocytes, 15o (IC50 = 0.42 muM), antagonized NECA-induced stimulation of cyclic AMP production (IC50 = 0.063 muM). This inhibitory effect was much more potent than those of FK453, KF17837, and L249313 which have been reported to be respectively A(1), A(2A), and A(3) selective antagonists. These findings agree very well with the result that, compared to 15o, these selective antagonists for each receptor subtype showed only marginal effects in rat hepatocytes. These results suggest that adenosine agonist-induced glucose production in rat hepatocytes is mediated through the A(2B) receptor. Furthermore, 15o showed hypoglycemic activity in an animal model of noninsulin-dependent diabetes mellitus, the KK-A(y) mice. It is possible that inhibition of hepatic glucose production via the A(2B) receptor could be at least one of the mechanisms by which 15o exerts its in, vivo effects. Further elaboration of this group of compounds may afford novel antidiabetic agents.

  DOI：

  10.1021/jm990499b

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021239885A1

  公开（公告）日：2021-12-02

  The invention relates to novel compounds for use as inhibitors of NLRP3 inflammasone production, wherein such compounds are as defined by compounds of formula (I) and wherein the integers R1, R2 and R3 are defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of a disease or disorder that is associated with NLRP3 inflammasome activity.

  本发明涉及用于抑制NLRP3炎症体产生的新化合物，其中所述化合物由公式（I）定义，其中整数R1、R2和R3在描述中定义，且所述化合物可用作药物，例如用于治疗与NLRP3炎症体活性相关的一种疾病或失调。
• Universal Base
  申请人：Kataoka Masanori

  公开号：US20100036108A1

  公开（公告）日：2010-02-11

  The present invention provides artificial universal base capable of base pairing nonspecifically with any of four kinds of natural nucleic acid bases (A, T, G, and C) without the function to specifically recognize pairing natural nucleic acid bases for base pair formation. Universal base capable of base paring nonspecifically with four kinds of natural nucleic acid bases, wherein the universal base has a structure represented by the following chemical formula: wherein R represents a monovalent group other than a hydrogen atom.

  本发明提供了一种人工通用碱基，能够非特异性地与四种天然核酸碱基（A、T、G 和 C）中的任何一种进行碱基配对，而无需特异性识别配对天然核酸碱基以进行碱基配对形成。具有非特异性地与四种天然核酸碱基进行碱基配对的通用碱基，其中通用碱基具有以下化学式所代表的结构：其中 R 代表除氢原子以外的一价基团。
• Regioselective alkylation reaction of purines under microwave irradiation
  作者：Arturo Vinuesa、Miquel Viñas、Daniel Jahani、Jaume Ginard、Nuria Mur、Maria Dolors Pujol

  DOI：10.1002/jhet.4407

  日期：2022.3

  The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylation at N-7 and N-9. In this work, the reaction conditions have been optimized to obtain the alkylation products of N-9 regioselectively. Different

  通常在阴离子形成后通过用碱和烷基卤处理进行的嘌呤烷基化是复杂的，并且在最好的情况下，获得了N-烷基化化合物的混合物。嘌呤衍生物可以从N -7 和N -9 的烷基化中获得。在这项工作中，对反应条件进行了优化，以区域选择性地获得N -9 的烷基化产物。已经尝试了不同的碱，氢氧化四丁基铵产生了最好的结果。反应取决于所使用的碱和溶剂的类型，并且在使用微波辐照的帮助下显着改善，这也通过减少副产物的形成而显着减少了反应时间。
• The first total synthesis of heteromine B, and an improved synthesis of heteromine A; natural products with antitumor activities
  作者：Heidi Roggen、Colin Charnock、Lise-Lotte Gundersen

  DOI：10.1016/j.tet.2009.04.100

  日期：2009.7

  Efficient total syntheses of heteromines A and B (antitumor compounds previously isolated from the plant Heterostemma brownii Hayata) from commercially available 2-amino-6-chloropurine have been developed. The synthesis of heteromine A is considerably shorter than the previously reported synthesis, only requiring four steps, whereas the iodide salt of heteromine B was prepared in five steps. Heteromines

  已经开发了从可商购的2-氨基-6-氯嘌呤有效合成总的杂胺A和B（先前从植物杂种异叶菊（Heterostemma brownii Hayata）中分离的抗肿瘤化合物）。杂胺A的合成比以前报道的合成短得多，仅需要四个步骤，而杂胺B的碘盐是在五个步骤中制备的。异源A和B没有显示出明显的抗菌活性，因此对癌细胞系具有选择性。
• Tricyclic Purine Analogs Derived from 2-Amino-6-chloropurine and 2,6-Diaminopurine and Their Methylated Quaternary Salts
  作者：Kateřina Hořejší、Radek Pohl、Antonín Holý

  DOI：10.1135/cccc20060077

  日期：——

  A novel series of tricyclic, etheno-bridged purine analogs was sythesized from 2-amino-6-(substituted amino)-9-methylpurines by cyclization with chloroacetaldehyde, with particular focus on the regioselectivity of the cyclization reaction and fluorescence properties. The analogs as well as the starting purines were alkylated with iodomethane, affording a new class of quaternary salts with potential biological activity. Neither significant fluorescence nor cytostatic effect was found.

  一系列新型三环、乙烯桥联嘌呤类似物从2-氨基-6-(取代氨基)-9-甲基嘌呤通过与氯乙醛环化合成，特别关注环化反应的区域选择性和荧光性质。这些类似物以及起始嘌呤均与碘甲烷烷基化，形成一类具有潜在生物活性的季铵盐。未发现显著的荧光或细胞静止效应。