6-(4-bromophenyl)-3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-9-oxo-5H-imidazol[1,2-a]purine | 157892-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-bromophenyl)-3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-9-oxo-5H-imidazol[1,2-a]purine
• 英文别名: 6-(4-BrPh)-TRIC-ACV；6-(4-bromophenyl)-3-(2-hydroxyethoxymethyl)-5H-imidazo[1,2-a]purin-9-one
• CAS: 157892-01-8
• 化学式: C₁₆H₁₄BrN₅O₃
• 分子量: 404.223
• InChiKey: NCNGTLPXBCQJKO-UHFFFAOYSA-N

物化性质

• 沸点：
  794.5±70.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-bromophenyl)-3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-9-oxo-5H-imidazol[1,2-a]purine 、 4-羟基苯硼酸频哪醇酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2-hydroxyethoxymethyl)-6-[4-(4-hydroxyphenyl)phenyl]-5H-imidazo[1,2-a]purin-9-one
  参考文献：
  名称：

  Synthesis and Fluorescent Properties of 6-(4-Biphenylyl)-3,9-dihydro-9-oxo-5H-imidazo[1,2-A]purine Analogues of Acyclovir and Ganciclovir

  摘要：

  Tricyclic (T) analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2) carrying the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system [i.e., 6-(4-BrPh)TACV, 5 and 6-(4-BrPh)TGCV, 6] were transformed into 6-[(4'-R-2)-4-biphenylyl] derivatives of TACV (7-9) and TGCV (10-12) by Suzuki cross coupling with 4-substituted phenylboronic acids. Compound 11 (R-2 = CH2OH) showed a high (similar to1000) selectivity index against herpes simplex virus type 1 (HSV-1) together with advantageous fluorescence properties (emission in visible region, little overlap with absorption and moderate intensity).

  DOI：

  10.1081/ncn-120022684
• 作为产物：
  描述：

  阿昔洛韦 、 2,4'-二溴苯乙酮 在 sodium hydride 、 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 6-(4-bromophenyl)-3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-9-oxo-5H-imidazol[1,2-a]purine
  参考文献：
  名称：

  Synthesis and Fluorescent Properties of 6-(4-Biphenylyl)-3,9-dihydro-9-oxo-5H-imidazo[1,2-A]purine Analogues of Acyclovir and Ganciclovir

  摘要：

  Tricyclic (T) analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2) carrying the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system [i.e., 6-(4-BrPh)TACV, 5 and 6-(4-BrPh)TGCV, 6] were transformed into 6-[(4'-R-2)-4-biphenylyl] derivatives of TACV (7-9) and TGCV (10-12) by Suzuki cross coupling with 4-substituted phenylboronic acids. Compound 11 (R-2 = CH2OH) showed a high (similar to1000) selectivity index against herpes simplex virus type 1 (HSV-1) together with advantageous fluorescence properties (emission in visible region, little overlap with absorption and moderate intensity).

  DOI：

  10.1081/ncn-120022684

文献信息

• Fused tri-heterocyclic compounds
  申请人：——

  公开号：US20030105116A1

  公开（公告）日：2003-06-05

  Fused tri-heterocyclic compounds of formula: 1 R 1 is H or alkyl; R 2 is H, alkyl, alkenyl, aryl, heteroaryl, cyclyl, or heterocyclyl; R 3 and R 4 , independently, is H, alkyl, alkenyl, aryl, heteroaryl, cyclyl, heterocyclyl, or (CR a R b ) m X(CR c R d ) n Y; in which X is a bond, O, S, or NR e ; Y is alkoxy, aryloxy, heteroaryloxy, OC(O)R e , C(O)R e , N(R e R e′ ), NR e C(O)R e′ , S(O) 2 R e , or SR e ; each of m and n, independently, is 1, 2, 3, 4, or 5; each of R a , R b , R c , R d , R e , and R e′ , independently, is H, alkyl, aryl, heteroaryl, cyclyl, or heterocyclyl; and R 5 is H or halogen.

  化合物公式为：1R1为H或烷基；R2为H、烷基、烯基、芳基、杂芳基、环基或杂环基；R3和R4独立地为H、烷基、烯基、芳基、杂芳基、环基、杂环基或(CRaRb)mX(CRcRd)nY；其中X为键、O、S或NRe；Y为烷氧基、芳氧基、杂芳氧基、OC(O)Re、C(O)Re、N(ReRe′)、NReC(O)Re′、S(O)2Re或SRe；m和n分别独立地为1、2、3、4或5；Ra、Rb、Rc、Rd、Re和Re′各自独立地为H、烷基、芳基、杂芳基、环基或杂环基；R5为H或卤素。
• 9H-imidazo[1,2-a]purin-9-one compounds
  申请人：Lee Fang Yu

  公开号：US06887997B2

  公开（公告）日：2005-05-03

  Fused tri-heterocyclic compounds of formula: R 1 is H or alkyl; R 2 is H, alkyl, alkenyl, aryl, heteroaryl, cyclyl, or heterocyclyl; R 3 and R 4 , independently, is H, alkyl, alkenyl, aryl, heteroaryl, cyclyl, heterocyclyl, or (CR a R b ) m X(CR c R d ) n Y; in which X is a bond, O, S, or NR e ; Y is alkoxy, aryloxy, heteroaryloxy, OC(O)R e , C(O)R e , N(R e R e′ ), NR e C(O)R e′ , S(O) 2 R e , or SR e ; each of m and n, independently, is 1, 2, 3, 4, or 5; each of R a , R b , R c , R d , R e , and R e′ , independently, is H, alkyl, aryl, heteroaryl, cyclyl, or heterocyclyl; and R 5 is H or halogen.

  式子为：R1为氢或烷基; R2为氢、烷基、烯基、芳基、杂芳基、环基或杂环基; R3和R4分别为氢、烷基、烯基、芳基、杂芳基、环基、杂环基或(CRaRb)mX(CRcRd)nY; 其中X为键、O、S或NRe; Y为烷氧基、芳氧基、杂芳氧基、OC(O)Re、C(O)Re、N(ReRe′)、NReC(O)Re′、S(O)2Re或SRe; m和n分别为1、2、3、4或5; Ra、Rb、Rc、Rd、Re和Re′分别为氢、烷基、芳基、杂芳基、环基或杂环基; R5为氢或卤素。
• Fused tricyclic analogues of guanosine for treating tumors
  申请人：Yung Shin Pharmaceutical Ind. Co., Ltd.

  公开号：EP1270008A2

  公开（公告）日：2003-01-02

  Fused tri-heterocyclic compounds of formula: R1 is H or alkyl; R2 is H, alkyl, alkenyl, aryl, heteroaryl, cyclyl, or heterocyclyl; R3 and R4, independently, is H, alkyl, alkenyl, aryl, heteroaryl, cyclyl, heterocyclyl, or (CRaRb)mX(CRcRd)nY; in which X is a bond, O, S, or NRe; Y is alkoxy, aryloxy, heteroaryloxy, OC(O)Re, C(O)Re, N(ReRe'), NReC(O)Re', S(O)2Re, or SRe; each of m and n, independently, is 1, 2, 3, 4, or 5; each of Ra, Rb, Rc, Rd, Re, and Re', independently, is H, alkyl, aryl, heteroaryl, cyclyl, or heterocyclyl; and R5 is H or halogen.

  式中的融合三杂环化合物： R1 是 H 或烷基；R2 是 H、烷基、烯基、芳基、杂芳基、环烷基或杂环烷基；R3 和 R4 独立地是 H、烷基、烯基、芳基、杂芳基、环烷基、杂环烷基或 (CRaRb)mX(CRcRd)nY；其中 X 是键、O、S 或 NRe；Y是烷氧基、芳氧基、杂芳氧基、OC(O)Re、C(O)Re、N(ReRe')、NReC(O)Re'、S(O)2Re或SRe；m和n各自独立地为1、2、3、4或5；Ra、Rb、Rc、Rd、Re和Re'各自独立地为H、烷基、芳基、杂芳基、环烷基或杂环烷基；以及R5是H或卤素。
• Tricyclic Analogs of Acyclovir and Ganciclovir. Influence of Substituents in the Heterocyclic Moiety on the Antiviral Activity
  作者：Bozenna Golankiewicz、Tomasz Ostrowski、Graciela Andrei、Robert Snoeck、Erik De Clercq

  DOI：10.1021/jm00045a025

  日期：1994.9

  The effect of substitution in the tricyclic moiety of 3,9-dihydro-9-oxo-5H-imidazo[1,2-alpha]purine (1,N-2-ethenoguanine) analogues of acyclovir (1) and ganciclovir (2) on their physical properties and antiherpetic activity was investigated by synthesizing a series of compounds substituted in the 2, 6, or 7 position (6-14). Substitution in the 6-position with phenyl or 4-biphenylyl resulted in fluorescent compounds (7, 9, 13, 14). In general, the substituent in the 6 position potentiated the antiviral activity. The fluorescent 6-phenyl derivatives: 3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-9-oxo-6-phenyl- 5H-imidazo[1,2-alpha]purine (7) and its 3-[( 1,3-dihydroxy-2-propoxy)methyl] congener (13) were the most potent tricyclic analogues of 1 and 2, respectively. Compound 7 was inhibitory to TK+ HSV-1, TK+ HSV-2, and TK+ VZV within the concentration range of 0.2-2.0 mu g/mL, well below the cytotoxicity threshold (50 to > 100 mu g/mL). Compound 13 was inhibitory to TK+ HSV-1 and TK+ HSV-2 within the concentration range of 0.005-0.3 mu g/mL and to TK+ and TK- VZV within the concentration range of 0.4-3 mu g/mL (cytotoxicity threshold > 200 mu g/mL). Both 7 and 13 seem to be promising candidate compounds for the noninvasive diagnosis of herpesvirus infections.
• US6887997B2
  申请人：——

  公开号：US6887997B2

  公开（公告）日：2005-05-03