2-氯-6-甲氧基嘌呤 | 1198-46-5

• 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: 2-氯-6-甲氧基嘌呤
• 英文名称: 2-chloro-6-methoxy-9H-purine
• 英文别名: 2-Chlor-6-methoxy-purin；2-Chloro-6-methoxypurine；2-chloro-6-methoxy-7H-purine
• CAS: 1198-46-5
• 化学式: C₆H₅ClN₄O
• 分子量: 184.585
• InChiKey: MTDSMFYWSAISJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  2-氯-6-甲氧基嘌呤 生成 7-(2-bromoethyl)-2-chloro-6-methoxypurine
  参考文献：
  名称：

  SELECTIVE ANTIBACTERIALS FOR CLOSTRIDIUM DIFFICILE INFECTIONS

  摘要：

  这项发明涉及公式（I）的化合物：这些化合物可用作抗菌剂，特别是用于治疗与难辨梭菌相关的疾病。

  公开号：

  US20120232077A1
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 AMINOHIPPURATE SODIUM 作用下， 以68.26%的产率得到2-氯-6-甲氧基嘌呤
  参考文献：
  名称：

  Deuterium-Substituted 7-Substituted-2-(Benzylamino)-6-Ozopurine Compounds and Uses Thereof

  摘要：

  这项发明涉及公式（I）的化合物：这些化合物可用作抗菌剂，特别是用于对抗Clostridium difficile相关疾病。

  公开号：

  US20220024925A1

文献信息

• Synthesis and Cytotoxic Activity of Some New 2,6-Substituted Purines
  作者：Nageswara Rao Kode、Shashikant Phadtare

  DOI：10.3390/molecules16075840

  日期：——

  A seriesof twenty four acyclic unsaturated 2,6-substututed purines 5a-20b were synthesized. These compounds were evaluated for cytotoxic activity against NCI-60 DTP human tumor cell line screen at 10µMconcentration. N9-[(Z)-4'-chloro-2'-butenyl-1'-yl]-2,6-dichloropurine(5a), N9-[4'-chloro-2'-butynyl-1'-yl]-2,6-dichloropurine(10a), N9-[(E)-2',3'-dibromo-4'-chloro-2'-butenyl-1'-yl]-6-methoxypurine(14)and N9-[4'-chloro-2'-butynyl-1'-yl]-6-(4-methoxyphenyl)-purine(19)exhibited highly potent cytotoxic activity with GI50 values in the 1–5 µM range for most human tumor cell lines. Other compounds exhibited moderate activity.

  共合成了24种非环状不饱和2,6-取代嘌呤衍生物5a-20b。这些化合物在10微摩尔浓度下，针对NCI-60 DTP人肿瘤细胞系进行了细胞毒活性评估。其中，N9-[(Z)-4'-氯-2'-丁烯-1'-基]-2,6-二氯嘌呤(5a)、N9-[4'-氯-2'-丁炔-1'-基]-2,6-二氯嘌呤(10a)、N9-[(E)-2',3'-二溴-4'-氯-2'-丁烯-1'-基]-6-甲氧基嘌呤(14)以及N9-[4'-氯-2'-丁炔-1'-基]-6-(4-甲氧苯基)嘌呤(19)显示出极强的细胞毒活性，对大多数人肿瘤细胞系的GI50值在1至5微摩尔范围内。其他化合物表现出中等活性。
• CuBr Catalyzed C–N cross coupling reaction of purines and diaryliodonium salts to 9-arylpurines
  作者：Hong-Ying Niu、Chao Xia、Gui-Rong Qu、Qian Zhang、Yi Jiang、Run-Ze Mao、De-Yang Li、Hai-Ming Guo

  DOI：10.1039/c1ob05333g

  日期：——

  CuBr was found to be an efficient catalyst for the C–N cross coupling reaction of purine and diaryliodonium salts. 9-Arylpurines were synthesized in excellent yields with short reaction times (2.5 h). The method represents an alternative to the synthesis of 9-arylpurines viaCu(II) catalyzed C–N coupling reaction with arylboronic acids as arylating agents.

  CuBr被发现是嘌呤盐和二芳基碘鎓盐的C–N交叉偶联反应的有效催化剂。9-芳基嘌呤以极短的反应时间（2.5h）以优异的产率合成。该方法是通过以芳基硼酸为芳基化剂的Cu（II）催化的C–N偶联反应合成9-芳基嘌呤的替代方法。
• [EN] NUCLEOSIDE AND NUCLEOTIDE ANALOGUES BEARING A QUATERNARY ALL-CARBON STEREOGENIC CENTER AT THE 2' POSITION AND METHODS OF USE AS A CARDIOPROTECTIVE AGENT<br/>[FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES PORTANT UN CENTRE STÉRÉOGÈNE TOUT CARBONE QUATERNAIRE EN POSITION 2' ET PROCÉDÉS D'UTILISATION EN TANT QU'AGENT CARDIOPROTECTEUR
  申请人：LCB PHARMA INC

  公开号：WO2018049534A1

  公开（公告）日：2018-03-22

  Nucleoside and nucleotide analogues that can be used as cardioprotective agents are provided. The nucleosides and nucleotide analogues comprise tetrahydrofuranyl or tetrahydrothienyl moieties with quaternary stereogenic all-carbon centers at the 2' position and a phosphonate ester at the 5' position.

  提供可用作心脏保护剂的核苷和核苷酸类似物。这些核苷和核苷酸类似物包括在2'位置具有四氢呋喃基或四氢噻吩基的四面体立体异构所有碳中心，以及在5'位置具有磷酸酯基。
• Stereocontrolled approach for the syntheses of 3-isopurine nucleosides: 3-(2-deoxy-β-d-ribofuranosyl)xanthine and isoguanine by intramolecular glycosylation
  作者：Hideyuki Sugimura、Sho Endo、Ken Ishizuka

  DOI：10.1016/j.tetlet.2015.09.045

  日期：2015.10

  3-Isopurine nucleosides, namely 3-(ribofuranosyl)purine nucleosides, are interesting owing to their potential biological activity and as components of modified oligonucleotides. A regio- and stereocontrolled method was developed for the synthesis of β-2′-deoxy-3-isopurine nucleosides using the intramolecular glycosylation protocol. The availability of this method was shown by the first chemical synthesis

  3-异嘌呤核苷，即3-（呋喃呋喃糖基）嘌呤核苷，由于其潜在的生物学活性并作为修饰的寡核苷酸的组分，因此是令人感兴趣的。开发了区域和立体控制的方法，用于使用分子内糖基化方案合成β-2'-脱氧-3-异嘌呤核苷。通过3-（2-脱氧-β - d-核呋喃呋喃糖基）黄嘌呤和异鸟嘌呤的第一化学合成显示了该方法的可用性。
• Synthesis of Some Biologically Active Halogenopurines
  作者：Hu, Yu Lin、Liu, Xiang、Lu, Ming、Ge, Qiang、Liu, Xiao Bin

  DOI：10.5012/jkcs.2010.54.4.429

  日期：2010.8.20

  Guanine (1)으로부터 생물활성이 있는 halogenopurines계 화합물을 합성하였다. Guanine을 acetic anhydride와 반응시켜서 2,9-diacetylguanine (2-1)을 합성하여 얻어진 화합물을 $POCl_3$와 반응시켜서 화합물 3a를 합성하고, 다음 단계에서 2-amino-6-halogenopurines (3b-d)를 합성하였다. 2-Halogenopurines (2-2a-d, 4-2a-d, 5a-d)을 2-amino-6-substituted purines (1, 3a, 4-1)로부터 효율적으로 합성한 후에, 새로운 화합물인 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c 및 5d를 합성하였다. 합성한 화합물의 구조를 원소분석, $^1H$ NMR, mass spectral data로 확인하였으며, 합성한 화합물에 대한 항균 활성을 시험하였다. A series of some biologically active halogenopurines were synthesized from commercially available guanine (1). The reaction of guanine with acetic anhydride yielded 2,9-diacetylguanine (2-1) by acetylation reaction. Further treatment of 2-1 with $POCl_3$ by PEG-2000 phase transfer catalysis furnished the important compound 3a, then 2-amino-6-halogenopurines (3b-d) were obtained through chlorine-exchange halogenations between KX and 3a by TPPB phase transfer catalyst. Further, 2-halogenopurines (2-2a-d, 4-2a-d, 5a-d) were efficiently prepared from 2-amino-6-substituted purines (1, 3a, 4-1) via a diazotization catalyzed by their corresponding CuX, and some new compounds 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c and 5d have been discovered. The structures of synthesized compounds were mainly established on the basis of their elemental analysis, $^1H$ NMR, as well as their mass spectral data. All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activity.

  鸟嘌呤 (1)으로부터 생물활성이 있는 卤嘌呤 계화합물을 합성하였다.Guanine을 acetic anhydride와 반응시켜서 2,9-diacetylguanine (2-1)을 합성하여 얻어진 화합물을 $POCl_3$와 반응시켜서 화합물 3a를 합성하고, 다음 단계에서 2-amino-6-halogenopurines (3b-d)를 합성하였다.2-amino-6-substituted purines (1, 3a, 4-1)로부터 효율적으로 합성한 후에, 새로운 화합물인 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c 및 5d를 합성하였다.합성한 화합물의 구조를 원소분석, $^1H$ NMR, mass spectral data로 확인하였으며, 합성한 화합물에 대한 항균 활성을 시험하였다. 利用市售鸟嘌呤合成了一系列具有生物活性的卤代嘌呤 (1)。鸟嘌呤与乙酸酐反应，通过乙酰化反应得到 2,9-二乙酰鸟嘌呤（2-1）。在 PEG-2000 相转移催化剂的作用下，2-1 与 $POCl_3$ 进一步处理，得到了重要的化合物 3a，然后在 TPPB 相转移催化剂的作用下，通过 KX 与 3a 之间的氯交换卤化反应，得到了 2-氨基-6-卤代嘌呤（3b-d）。在相应的 CuX 催化下，2-氨基-6-取代嘌呤（1、3a、4-1）通过重氮化反应有效地制备了 2-卤代嘌呤（2-2a-d、4-2a-d、5a-d），并发现了一些新化合物 2-2a、2-2c、2-2d、4-2c、4-2d、5b、5c 和 5d。合成化合物的结构主要是根据其元素分析、$^1H$核磁共振以及质谱数据确定的。对所有标题化合物进行了抗真菌活性筛选，其中一些化合物显示出良好的活性。

表征谱图