2-Amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one | 130466-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-Amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one
• 英文别名: 9-(2',3'-Bis(hydroxymethyl)cyclobutyl)guanine；9-[2,3-bis(hydroxymethyl)cyclobutan-1-yl]guanine；(1α,2β,3α)-9-[2,3-Bis(hydroxymethyl)-cyclobutyl]guanine；2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-3H-purin-6-one；2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1H-purin-6-one
• CAS: 130466-27-2
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: GWFOVSGRNGAGDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one 、 [(1R,2S,4S)-2-(6-氨基嘌呤-9-基)-4-(羟基甲基)环丁基]甲醇 生成 9-(2'-(Hydroxymethyl)-3'-methylcyclobutyl)adenine
  参考文献：
  名称：

  Process for preparation of intermediates of carbocyclic nucleoside

  摘要：

  该化合物的化学式为：##STR1## 其中A是嘌呤-9-基团，嘌呤-9-基团的杂环同分异构体，嘧啶-1-基团或嘧啶-1-基团的杂环同分异构体；E是氢，-CH.sub.2 OH或-OH；G和D分别选择自氢，C.sub.1到C.sub.10烷基，-OH，-CH.sub.2 OH，-CH.sub.2 OR.sub.20，其中R.sub.20是C.sub.1到C.sub.6烷基，-CH.sub.2 OC(O)R.sub.21，其中R.sub.21是C.sub.1到C.sub.10烷基，-CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23)，其中R.sub.22是任何天然氨基酸的侧链，R.sub.23是氢或-C(O)CH(R.sub.24)(NH.sub.2)，其中R.sub.24是任何天然氨基酸的侧链，-CH.sub.1 SH，-Ch.sub.2 Cl，-Ch.sub.2 F，-CH.sub.2 Br，-CH.sub.2 I，-C(O)H，-CH.sub.2 CN，-CH.sub.2 N.sub.3，-CH.sub.2 NR.sub.1 R.sub.2，-CO.sub.2 R.sub.1，-CH.sub.2 CH.sub.2 OH，-CH.sub.2 CH.sub.2 OR.sub.20，其中R.sub.20如上定义，-CH.sub.2 CH.sub.2 OC(O)R.sub.21，其中R.sub.21如上定义，-CH.sub.2 CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23)，其中R.sub.22和R.sub.23如上定义，-CH.sub.2 CH.sub.2 PO.sub.3 H.sub.2，-Ch.sub.2 OPO.sub.3 H.sub.2，-OCH.sub.2 PO.sub.3 H.sub.2和-CH.sub.2 CO.sub.2 R.sub.3，其中R.sub.1和R.sub.2分别选择自氢和C.sub.1到C.sub.10烷基，R.sub.3是氢，C.sub.1到C.sub.10烷基，羧基烷基或氨基烷基；或其药用可接受盐。

  公开号：

  US05153352A1
• 作为产物：
  描述：

  [3-(2-Amino-6-phenylmethoxypurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate 、 甲醇 、 sodium methylate 、 盐酸 生成 2-Amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one
  参考文献：
  名称：

  SLUSARCHYK, W. A.;YOUNG, M. G.;BISACCHI, G. S.;HOCKSTEIN, D. R.;ZAHLER, R+, TETRAHEDRON. LETT., 30,(1989) N7, C. 6453-6456

  摘要：

  DOI：

文献信息

• Nucleotide mimics and their prodrugs
  申请人：——

  公开号：US20040059104A1

  公开（公告）日：2004-03-25

  The present invention relates to nucleoside diphosphate mimics and nucleoside triphosphate mimics, which contain diphosphate or triphosphate moiety mimics and optionally sugar-modifications and/or base-modifications. The nucleotide mimics of the present invention, in a form of a pharmaceutically acceptable salt, a pharmaceutically acceptable prodrug, or a pharmaceutical formulation, are useful as antiviral, antimicrobial, and anticancer agents. The present invention provides a method for the treatment of viral infections, microbial infections, and proliferative disorders. The present invention also relates to pharmaceutical compositions comprising the compounds of the present invention optionally in combination with other pharmaceutically active agents.

  本发明涉及核苷二磷酸模拟物和核苷三磷酸模拟物，其中包含二磷酸或三磷酸基团模拟物，以及可选的糖修饰和/或碱基修饰。本发明的核苷酸模拟物，以药学上可接受的盐、药学上可接受的前药或药物配方的形式，可用作抗病毒、抗微生物和抗癌剂。本发明提供了一种治疗病毒感染、微生物感染和增生性疾病的方法。本发明还涉及包含本发明化合物的药物组合物，可选地与其他药理活性剂结合。
• [EN] NOVEL PHOSPH(ON)ATE- AND SULF(ON)ATE-BASED PHOSPHATE MODIFIED NUCLEOSIDES USEFUL AS SUBSTRATES FOR POLYMERASES AND AS ANTIVIRAL AGENTS<br/>[FR] NOUVEAUX NUCLÉOSIDES MODIFIÉS AVEC UN PHOSPHATE, À BASE DE PHOSPH(ON)ATE ET DE SULF(ON)ATE, UTILES COMME SUBSTRATS POUR LES POLYMÉRASES ET COMME AGENTS ANTIVIRAUX
  申请人：UNIV LEUVEN KATH

  公开号：WO2011069688A1

  公开（公告）日：2011-06-16

  This invention provides phosphate-modified nucleosides represented by the structural formula ( I ): wherein W is O or S, and wherein B, R1; R3 and R2. are as defined herein. These compounds are useful as substrates for DNA/RNA polymerases, and as anti-viral agents in particular against HIV-1.

  这项发明提供了由结构式（I）表示的磷酸酯修饰核苷，其中W为O或S，B、R1、R3和R2的定义如本文所述。这些化合物可作为DNA/RNA聚合酶的底物使用，特别是作为抗HIV-1的抗病毒药物。
• NOVEL PHOSPH(ON)ATE- AND SULF(ON)ATE-BASED PHOSPHATE MODIFIED NUCLEOSIDES USEFUL AS SUBSTRATES FOR POLYMERASES AND AS ANTIVIRAL AGENTS
  申请人：Herdewijn Piet

  公开号：US20120245029A1

  公开（公告）日：2012-09-27

  This invention provides phosphate-modified nucleosides represented by the structural formula (I): wherein W is O or S, and wherein B, R 1 ; R 3 and R 2 . are as defined herein. These compounds are useful as substrates for DNA/RNA polymerases, and as anti-viral agents in particular against HIV-1.

  这项发明提供了由结构式(I)表示的磷酸修饰核苷酸，其中W为O或S，而B、R1、R2和R3如此处所定义。这些化合物可作为DNA/RNA聚合酶的底物，特别是在抗击HIV-1方面作为抗病毒剂。
• [EN] NOVEL SUBSTITUTED ARYL DERIVATIVES, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES AS ANTI-HIV AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS ARYLES SUBSTITUÉS, LEUR PROCÉDÉ DE PRÉPARATION ET LEURS UTILISATIONS THÉRAPEUTIQUES EN TANT QU'AGENTS ANTI-VIH
  申请人：CELLVIR

  公开号：WO2010066847A1

  公开（公告）日：2010-06-17

  The present invention concerns novel substituted aryl derivatives, their process of preparation and their use for inhibiting virus replication and for treating viral diseases or disorders such as HIV and/or HCV infection.

  本发明涉及新型取代芳基衍生物，其制备方法以及用于抑制病毒复制和治疗病毒性疾病或障碍，如HIV和/或HCV感染的用途。
• Process and intermediates for the preparation of an antiviral agent containing a cyclobutyl group
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0535448A2

  公开（公告）日：1993-04-07

  Racemic Feist's acid is treated with (R)-(+)-a-methylbenzylamine to yield (1R-trans)-3-methylenecyclopropane-1,2-dicarboxylic acid, (R)-a-methylbenzylamine (1:1) salt. This salt can then be converted to (1R-trans)-3-methylene-1,2-cyclopropanedicarboxylic acid, dimethyl ester which is an intermediate in the preparation of the antiviral agent Ä1R-(1a,2b,3a)Ü-2-amino-9-Ä2,3-bis(hydroxymethyl)cyclobutylÜ-1,9-dihydro-6H-purin-6-one. The improved process also enables the recovery of racemic Feist's acid from the resolution.

  混合型的费斯特酸经过(R)-(+)-α-甲基苄胺的处理，生成(1R-trans)-3-亚甲基环丙烷-1,2-二羧酸，与(R)-α-甲基苄胺(1:1)盐。该盐可转化为(1R-trans)-3-亚甲基-1,2-环丙烷二羧酸，二甲酯，该中间体用于制备抗病毒剂Ä1R-(1a,2b,3a)Ü-2-氨基-9-Ä2,3-双(羟甲基)环丁基Ü-1,9-二氢-6H-嘌呤-6-酮。改进的工艺还能使费斯特酸从分离中恢复。