9-(3,4-二羟基丁基)鸟嘌呤 | 83470-64-8

• 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: 9-(3,4-二羟基丁基)鸟嘌呤
• 英文名称: 9-(3,4-dihydroxybutyl)guanine
• 英文别名: 9-(3,4-Dihydroxybutyl)guanine；2-amino-9-(3,4-dihydroxybutyl)-1H-purin-6-one
• CAS: 83470-64-8
• 化学式: C₉H₁₃N₅O₃
• 分子量: 239.234
• InChiKey: QOVUZUCXPAZXDZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  4-(2-amino-1,6-dihydro-6-oxopurin-9-yl)-2-hydroxybutyric acid ethyl ester 以 盐酸 、 水 、 异丙醇 为溶剂， 生成 9-(3,4-二羟基丁基)鸟嘌呤
  参考文献：
  名称：

  Derivatives of guanine for combating herpes virus infections

  摘要：

  该公式的新型抗病毒化合物为##STR1##其中R.sub.1和R.sub.2中的每一个，相同或不同，均为氢、羟基或氟；但是当R.sub.1和R.sub.2不同时，R.sub.1或R.sub.2为氢，当R.sub.1和R.sub.2相同时，R.sub.1和R.sub.2为羟基或氟；或其生理可接受的盐或其光学异构体，其制备方法，含有该化合物的药物制剂，以及用于治疗病毒感染和其他由病毒引起的疾病的方法。

  公开号：

  US04495190A1

文献信息

• Novel phosphonic acid based prodrugs of PMEA and its analogues
  申请人：——

  公开号：US20030229225A1

  公开（公告）日：2003-12-11

  Prodrugs of Formula I, their uses, their intermediates, and their method of manufacture are described: 1 wherein: M and V are cis to one another and MPO 3 H 2 is a phosphonic acid selected from the group consisting of 9-(2-phosphonylmethoxyethyl)adenine, (R)-9-(2-phosphonylmethoxy propyl)adenine, 9-(2-phosphonylmethoxyethyl)guanine, 9-(2-phosphonylmethoxy ethyloxy)adenine, 9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine, (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine, 9-(3-hydroxy-2-phosphonylmethoxypropyl)guanine, and (S)-9-(3-fluoro-2-phosphonyl methoxypropyl)adenine; V is selected from a group consisting of phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, 3-furanyl, 2-thienyl, and 3-thienyl, all optionally substituted with 1-3 substituents selected from a group consisting of F, Cl, Br, C1-C3 alkyl, CF 3 and OR 6 ; R6 is selected from the group consisting of C1-C3 alkyl, and CF 3 ; and pharmaceutically acceptable salts thereof.

  公式I的前药、它们的用途、它们的中间体以及它们的制造方法被描述：其中：M和V相对于彼此是顺式的，MPO3H2是从以下组中选择的膦酸，包括9-(2-膦甲氧基乙基)腺嘌呤，(R)-9-(2-膦甲氧基丙基)腺嘌呤，9-(2-膦甲氧基乙基)鸟嘌呤，9-(2-膦甲氧基乙氧基)腺嘌呤，9-(2-膦甲氧基乙基)-2,6-二氨基嘌呤，(S)-1-(3-羟基-2-膦甲氧基丙基)胞嘧啶，(S)-9-(3-羟基-2-膦甲氧基丙基)腺嘌呤，9-(3-羟基-2-膦甲氧基丙基)鸟嘌呤，以及(S)-9-(3-氟-2-膦甲氧基丙基)腺嘌呤；V从以下组中选择，包括苯基，2-吡啶基，3-吡啶基，4-吡啶基，2-呋喃基，3-呋喃基，2-噻吩基和3-噻吩基，所有这些基可选地被1-3个来自F、Cl、Br、C1-C3烷基、CF3和OR6的基替代；R6从C1-C3烷基和CF3的组中选择；以及其药学上可接受的盐。
• Non nucleoside reverse transcriptase inhibitors
  申请人：Chen M. James

  公开号：US20060128692A1

  公开（公告）日：2006-06-15

  Phosphorus-substituted imidazole compounds with anti-HIV properties having use as therapeutics and for other industrial purposes are disclosed. The compositions inhibit reverse transcriptase activity and are useful therapeutically for the inhibition of such enzymes, as well as in assays for the detection of such enzymes.

  本发明揭示了具有抗HIV特性的磷替代咪唑化合物，其具有作为治疗剂和其他工业用途的用途。这些组合物抑制反转录酶活性，可用于治疗抑制该类酶以及用于检测该类酶的测定。
• Pyrimidyl phosphonate antiviral compounds and methods of use
  申请人：Jin Haolun

  公开号：US20050282839A1

  公开（公告）日：2005-12-22

  Pyrimidine I and pyrimidinone II phosphonate compounds and methods for viral inhibition are disclosed. The compounds include at least one phosphonate group covalently attached at any site.

  本发明揭示了嘧啶I和嘧啶酮II膦酸酯化合物及其用于病毒抑制的方法。这些化合物包括至少一个膦酸酯基固定在任何位置上。
• Phosphonate analogs of HIV integrase inhibitor compounds
  申请人：Cai R. Zhenhong

  公开号：US20060116356A1

  公开（公告）日：2006-06-01

  Novel HIV integrase inhibitor compounds having at least one phosphonate group, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.

  本发明揭示了至少具有一个膦酸酯基团的新型HIV整合酶抑制剂化合物，其保护中间体以及用于抑制HIV整合酶的方法。
• Novel prodrugs for phosphorus-containing compounds
  申请人：——

  公开号：US20020052345A1

  公开（公告）日：2002-05-02

  Prodrugs of formula I, their uses, their intermediates, and their method of manufacture are described: 1 wherein: V, W, and W′ are independently selected from the group consisting of —H, alkyl, aralkyl, alicyclic, aryl, substituted aryl, heteroaryl, substituted heteroaryl, 1-alkenyl, and 1-alkynyl; or together V and Z are connected via an additional 3-5 atoms to form a cyclic group containing 5-7 atoms, optionally 1 heteroatom, substituted with hydroxy, acyloxy, alkoxycarbonyloxy, or aryloxycarbonyloxy attached to a carbon atom that is three atoms from both O groups attached to the phosphorus; or together V and Z are connected via an additional 3-5 atoms to form a cyclic group, optionally containing 1 heteroatom, that is fused to an aryl group at the beta and gamma position to the O attached to the phosphorus; together V and W are connected via an additional 3 carbon atoms to form an optionally substituted cyclic group containing 6 carbon atoms and substituted with one substituent selected from the group consisting of hydroxy, acyloxy, alkoxycarbonyloxy, alkylthiocarbonyloxy, and aryloxycarbonyloxy, attached to one of said carbon atoms that is three atoms from an O attached to the phosphorus; together Z and W are connected via an additional 3-5 atoms to form a cyclic group, optionally containing one heteroatom, and V must be aryl, substituted aryl, heteroaryl, or substituted heteroaryl; together W and W′ are connected via an additional 2-5 atoms to form a cyclic group, optionally containing 0-2 heteroatoms, and V must be aryl, substituted aryl, heteroaryl, or substituted heteroaryl; Z is selected from the group consisting of —CHR 2 OH, —CHR 2 OC(O)R 3 , —CHR 2 OC(S)R 3 , —CHR 2 OC(S)OR 3 , —CHR 2 OC(O)SR 3 , —CHR 2 OCO 2 R 3 , —OR 2 , —SR 2 , —CHR 2 N 3 , —CH 2 aryl, —CH(aryl)OH, —CH(CH═CR 2 2)OH, —CH(C≡CR 2 )OH, —R 2 , —NR 2 2 , —OCOR 3 , —OCO 2 R 3 , —SCOR 3 , —SCO 2 R 3 , —NHCOR 2 , —NHCO 2 R 3 , —CH 2 NHaryl, —(CH 2 ) p — OR 12 , and —(CH 2 ) p —SR 12 ; p is an integer 2 or 3; with the provisos that: a) V, Z, W, W′ are not all —H; and b) when Z is —R 2 , then at least one of V, W, and W′ is not —H, alkyl, aralkyl, or alicyclic; R 2 is selected from the group consisting of R 3 and —H; R 3 is selected from the group consisting of alkyl, aryl, alicyclic, and aralkyl; R 12 is selected from the group consisting of —H, and lower acyl; M is selected from the group that attached to PO 3 2− , P 2 O 6 3− , or P 3 O 9 4− is a biologically active agent, and is attached to the phosphorus in formula I via a carbon, oxygen, sulfur or nitrogen atom; and pharmaceutically acceptable prodrugs and salts thereof.

  本文描述了式I的前药、其用途、其中间体及其制备方法：其中：V、W和W′独立地选自由—H、烷基、芳基烷基、脂环烷基、芳香族、取代芳基、杂芳基、取代杂芳基、1-烯基和1-炔基组成的群体；或者V和Z通过额外的3-5个原子连接形成含有5-7个原子的环状基团，可选地含有1个杂原子，取代为羟基、酰氧基、烷氧羰氧基或芳氧羰氧基，连接到距离磷的两个O基团都有3个原子的碳原子上；或者V和Z通过额外的3-5个原子连接形成一个环状基团，可选地含有1个杂原子，融合到与连接到磷的O的β和γ位的芳基团上；或者V和W通过额外的3个碳原子连接形成一个可选地取代的含有6个碳原子的环状基团，并取代有来自羟基、酰氧基、烷氧羰氧基、烷基硫酰氧基和芳基羰氧基的一种取代基，连接到距离磷的一个O上的碳原子上；或者Z和W通过额外的3-5个原子连接形成一个环状基团，可选地含有一个杂原子，且V必须是芳基、取代芳基、杂芳基或取代杂芳基；或者W和W′通过额外的2-5个原子连接形成一个环状基团，可选地含有0-2个杂原子，且V必须是芳基、取代芳基、杂芳基或取代杂芳基；Z选自由—CHR2OH、—CHR2OC（O）R3、—CHR2OC（S）R3、—CHR2OC（S）OR3、—CHR2OC（O）SR3、—CHR2OCO2R3、—OR2、—SR2、—CHR2N3、—CH2芳基、—CH（芳基）OH、—CH（CH═CR22）OH、—CH（C≡CR2）OH、—R2、—NR22、—OCOR3、—OCO2R3、—SCOR3、—SCO2R3、—NHCOR2、—NHCO2R3、—CH2NH芳基、—（CH2）p—OR12和—（CH2）p—SR12；p是整数2或3；具有以下限制条件：a）V、Z、W、W′不全为—H；b）当Z为—R2时，至少有一个V、W或W′不为—H、烷基、芳基烷基或脂环烷基；R2选自由R3和—H组成的群体；R3选自由烷基、芳基、脂环烷基和芳基烷基组成的群体；R12选自由—H和较低酰基组成的群体；M选自连接到PO32−、P2O63−或P3O94−的群体中的生物活性剂，并通过碳、氧、硫或氮原子连接到式I中的磷；以及其药学上可接受的前药和盐。