6-氨基-2-疏基嘌呤 | 3647-48-1

• 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-氨基-2-疏基嘌呤
• 英文名称: 6-aminopurine-2-thiol
• 英文别名: 6-amino-2-thiopurine；2-mercaptoadenine；2-thioadenine；6-amino-3,7(9)-dihydro-purine-2-thione；6-amino-2-mercaptopurine；6-Amino-purin-2-thiol；6-amino-1,7-dihydropurine-2-thione
• CAS: 3647-48-1
• 化学式: C₅H₅N₅S
• mdl: MFCD21333190
• 分子量: 167.194
• InChiKey: LQJZZLRZEPKRRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  273.3±50.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

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
  2,6-二巯基嘌呤	2,6-Dimercapto-purin	5437-25-2	C5H4N4S2	184.246

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  腺嘌呤	adenine	73-24-5	C5H5N5	135.128
  2-溴-6-氨基嘌呤	2-bromo-9H-purin-6-amine	28128-25-8	C5H4BrN5	214.024
  ——	2-Cyclopentylthioadenin	63177-72-0	C10H13N5S	235.313
  ——	2-(cyclohexylthio)-9H-purin-6-amine	63187-56-4	C11H15N5S	249.34
  ——	2-Cycloheptylthioadenin	63187-57-5	C12H17N5S	263.366

反应信息

• 作为反应物：
  描述：

  6-氨基-2-疏基嘌呤 在 5%-palladium/activated carbon 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以41.5%的产率得到腺嘌呤
  参考文献：
  名称：

  一种腺嘌呤的合成方法

  摘要：

  本发明公开了一种腺嘌呤的合成方法。本发明采用丙二腈和硫脲为原料，在醇钠的作用下进行环合反应，制得4,6‑二氨基‑2‑巯基嘧啶，然后经过三条反应路线，合成得到腺嘌呤。本发明方法虽然反应步骤较多，但每步反应产物无须精制和烘干，可直接投入下一步反应中，操作简便。所用原料易得，价格相对低廉，反应条件温和，操作简便，反应步骤减少，反应时间较短，总反应收率较高，适合工业化生产。

  公开号：

  CN103709164B
• 作为产物：
  描述：

  2-巯基-4,5,6-三氨基嘧啶 以16%的产率得到
  参考文献：
  名称：

  KIKUGAWA K.; SUEHIRO H.; AOKI A., CHEM. AND PHARM. BULL. , 1977, 25, NO 7, 1811-1821

  摘要：

  DOI：

文献信息

• Efficient Synthesis of Acyclic Nucleosides by N-Alkylation of Pyrimidine and Purine-bases Using a New Coupling Agent of Cesium Iodide
  作者：Yong Hae Kim、Joong Young Kim、Chun Ho Lee

  DOI：10.1246/cl.1988.1045

  日期：1988.6.5

  Acyclic nucleosides, ((1,3-bis(benzyloxy)-2-propoxy) methyl)-2-thio-pyrimidine, -uracil, -2-thiouracil, and -2-thioadenine, and (2-acetoxyethoxy methyl)-2-thioadenine, -2-thiopyrimidine, -uracil, and -2-thiouracil have been successfully synthesized in good yields by N-alkylations of the bases with the corresponding alkyl-acetate (2) and -chloride (3) using cesium iodide under neutral condition in acetonitrile.

  成功合成了无环核苷，包括((1,3-双(苄氧基)-2-丙氧基)甲基)-2-硫代吡啶、-尿嘧啶、-2-硫代尿嘧啶和-2-硫代腺嘌呤，以及(2-乙酰氧乙氧基甲基)-2-硫代腺嘌呤、-2-硫代吡啶、-尿嘧啶和-2-硫代尿嘧啶，合成方法为在中性条件下，使用碘化铯在乙腈中通过与相应的烷基乙酸酯(2)和烷基氯化物(3)进行N-烷基化反应，获得了良好的产量。
• Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases
  作者：Maria Spassova、Hana Dvořáková、Antonín Holý、Miloš Buděšínský、Milena Masojídková

  DOI：10.1135/cccc19941153

  日期：——

  Alkylation of heterocyclic bases with azidomethyloxirane (I) under basic catalysis with potassium or cesium carbonate afforded N-(3-azido-2-hydroxypropyl) derivatives II. Hydrogenation of these compounds over palladium on carbon gave the corresponding 3-amino-2-hydroxypropyl derivatives III. The same compounds III were prepared by alkylation of heterocyclic bases with phthalimidomethyloxirane (VII) in the presence of cesium carbonate and subsequent reaction of the formed N-(3-phthalimido-2-hydroxypropyl) derivatives VIII with hydrazine. The phthalimido derivatives VIII are easily hydrolyzed already in weakly alkaline aqueous medium to give 9-[3-(o-carboxybenzoylamino)-2-hydroxypropyl] derivatives IX and X.

  杂环碱与氮甲基环氧丙烷（I）在钾或铯碳酸盐的碱性催化下发生烷基化反应，形成N-(3-叠氮-2-羟基丙基)衍生物II。将这些化合物在钯碳上进行氢化反应，得到相应的3-氨基-2-羟基丙基衍生物III。同样的化合物III可通过在铯碳酸盐存在下，将杂环碱与邻苯二甲酰亚氨基环氧丙烷（VII）发生烷基化反应，并将形成的N-(3-邻苯二甲酰亚氨基-2-羟基丙基)衍生物VIII与联氨反应制备。邻苯二甲酰亚氨基衍生物VIII在弱碱性水介质中易于水解，形成9-[3-(邻二甲酰苯胺基)-2-羟基丙基]衍生物IX和X。
• Purine derivatives having phosphodiesterase iv inhibition activity
  申请人：Euro-Celtique, S.A.

  公开号：US06413975B1

  公开（公告）日：2002-07-02

  Disclosed are compounds of the formula: wherein R3, R6a, R6b and R8 are substituted as disclosed herein. The compounds are effective in effecting PDE IV inhibition in patients in need thereof.

  本发明涉及一种式子为：其中R3、R6a、R6b和R8如本文所述的取代基的化合物。这些化合物对于需要PDE IV抑制的患者具有有效作用。
• Purine derivatives having phosphodiesterase IV inhibition activity
  申请人：Euro-Celtique S.A.

  公开号：US06294541B1

  公开（公告）日：2001-09-25

  A compound of the formula: wherein R3 represent a C1-8 alkyl which is unbranched or branched and unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; C3-8 cycloalkyl which is unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; C4-8 cycloalkylalkyl wherein the cycloalkyl portion is unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; aryl which is unsubstituted or substituted with Cl, NH2, alkylamino, dialkylamino, amido, C1-C8 alkylamido, C1-C3 dialkylamido, OH, alkoxy, HC═NOH, HC═NOCONH2, C1-C3 alkyl, phenyl or benzyl; aralkyl (C1-4); heterocyclyl; heterocyclylalkyl (C1-C4); and heteroaryl; R8 represents H or a C1-8 alkyl which is unbranched or branched and unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; C3-8 cycloalkyl which is unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; C4-8 cycloalkylalkyl wherein the cycloalkyl portion is unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; aryl which is unsubstituted or substituted with Cl, NH2, alkylamino, dialkylamino, amido, C1-C8 alkylamido, C1-C3 dialkylamido, OH, alkoxy, HC═NOH, HC═NOCONH2, C1-C3 alkyl, phenyl or benzyl; aralkyl (C1-4); heterocyclyl; heterocyclylalkyl (C1-C4); and heteroaryl.

  一种化合物的化学式：其中R3代表C1-8烷基，该烷基是直链或支链的，未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；C3-8环烷基，未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；C4-8环烷基烷基，其中环烷基部分未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；苯基，未取代或取代为Cl、NH2、烷基氨基、二烷基氨基、酰胺、C1-C8烷基酰胺、C1-C3二烷基酰胺、OH、烷氧基、HC═NOH、HC═NOCONH2、C1-C3烷基、苯基或苄基；芳基烷基（C1-4）；杂环基；杂环基烷基（C1-C4）；和杂芳基。R8代表H或C1-8烷基，该烷基是直链或支链的，未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；C3-8环烷基，未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；C4-8环烷基烷基，其中环烷基部分未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；苯基，未取代或取代为Cl、NH2、烷基氨基、二烷基氨基、酰胺、C1-C8烷基酰胺、C1-C3二烷基酰胺、OH、烷氧基、HC═NOH、HC═NOCONH2、C1-C3烷基、苯基或苄基；芳基烷基（C1-4）；杂环基；杂环基烷基（C1-C4）；和杂芳基。
• Chemical compounds having PDE-IV inhibition activity
  申请人：Euro-Celtique, S.A.

  公开号：US05939422A1

  公开（公告）日：1999-08-17

  Disclosed is a compound of the formula (I): wherein R.sub.3, R.sub.6a and R.sub.8 are the same or different and represent a C.sub.2-8 alkyl which is unbranched or branched and unsubstituted or substituted; C.sub.3-8 cycloalkyl which is unsubstituted or substituted; C.sub.4-8 cycloalkylalkyl wherein the cycloalkyl portion is unsubstituted or substituted; aryl which is unsubstituted or substituted; aralkyl C.sub.1-4 ; heterocyclyl; and heterocyclylalkyl (C.sub.1 -C.sub.4) R.sub.6b represents H or R.sub.6a, or together R.sub.6b, N, and R.sub.6a make a C.sub.3 -C.sub.8 ring containing from one to three nitrogen atoms, from zero to two oxygen atoms, from zero to two sulfur atoms, which is optionally substituted; and where aryl is phenyl or naphthyl, the heterocyclyl is a 5, 6 or 7 membered ring including from one to three nitrogen atoms, and from zero to two oxygen atoms, from zero to two sulfur atoms, and can be substituted as in aryl on the carbons or nitrogens of that ring; or a pharmaceutically acceptable salt thereof.

  本发明揭示了一种化合物的结构式（I）：其中，R.sub.3、R.sub.6a和R.sub.8相同或不同，表示未支链或支链的C.sub.2-8烷基，未取代或取代；未取代或取代的C.sub.3-8环烷基；未取代或取代的C.sub.4-8环烷基烷基，其中环烷基部分未取代或取代；未取代或取代的芳基；未取代或取代的芳基烷基C.sub.1-4；杂环烷基；和杂环烷基烷基（C.sub.1-C.sub.4）；R.sub.6b表示H或R.sub.6a，或者R.sub.6b，N和R.sub.6a共同构成一个含有从1到3个氮原子，从0到2个氧原子，从0到2个硫原子的C.sub.3-C.sub.8环，该环可以选择性地被取代；其中，苯基或萘基的芳杂环为5、6或7成员环，包括从1到3个氮原子和从0到2个氧原子、从0到2个硫原子，并且可以在该环的碳或氮上像芳基一样被取代；或其药学上可接受的盐。