2-溴-2'-脱氧肌苷 | 123994-87-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 2-溴-2'-脱氧肌苷
• 英文名称: 2-bromo-2'-deoxyinosine
• 英文别名: 2-Bromo-2'-deoxyinosine；2-bromo-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 123994-87-6
• 化学式: C₁₀H₁₁BrN₄O₄
• 分子量: 331.126
• InChiKey: HGAZEBCPIVCHRO-KVQBGUIXSA-N

物化性质

• 密度：
  2.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-溴-2'-脱氧肌苷 在 一水合肼 作用下， 以 乙二醇甲醚 为溶剂， 反应 1.0h， 以60 mg的产率得到2-hydrazinodeoxyinosine
  参考文献：
  名称：

  鸟嘌呤的N2氨基化为2-肼基次黄嘌呤，这是一种由肝致癌物2-硝基丙烷产生的新型体内核酸修饰。

  摘要：

  2-硝基丙烷（一种工业化学品和大鼠中的肝致癌物）诱导芳基磺基转移酶介导的肝脏DNA和RNA碱基修饰[Sodum，RS，Sohn，OS，Nie，G.，and Fiala，ES（1994）。Res。毒药。7，344-351]。这些修饰中的两个先前被鉴定为8-氨基鸟嘌呤和8-氧代鸟嘌呤。我们现在报告，迄今尚未确定的第三种核酸修饰的基本部分，即RNA中的RX1和DNA中的DX1，是2-肼基次黄嘌呤（N2-氨基鸟嘌呤）。2-Hyrazrazinoinosine和2-hydrazinodeoxyinosine，是通过采用已公开的程序合成的，分别用2-硝基丙烷处理的大鼠的肝RNA和DNA的RX1和DX1进行共色谱。2-Hyrazrazinoinosine和2-hydrazinodeoxyinosine在溶液中像体内产物RX1和DX1一样不稳定。在中性pH下，次黄嘌呤核苷是分解的主要产物，而在pH等于或大

  DOI：

  10.1021/tx980160c
• 作为产物：
  描述：

  2-溴次黄嘌呤 、 beta-胸苷 在 purine nucleoside phosphorylase 、 thymidine phosphorylase 作用下， 以 phosphate buffer 为溶剂， 反应 20.0h， 以60%的产率得到2-溴-2'-脱氧肌苷
  参考文献：
  名称：

  鸟嘌呤的N2氨基化为2-肼基次黄嘌呤，这是一种由肝致癌物2-硝基丙烷产生的新型体内核酸修饰。

  摘要：

  2-硝基丙烷（一种工业化学品和大鼠中的肝致癌物）诱导芳基磺基转移酶介导的肝脏DNA和RNA碱基修饰[Sodum，RS，Sohn，OS，Nie，G.，and Fiala，ES（1994）。Res。毒药。7，344-351]。这些修饰中的两个先前被鉴定为8-氨基鸟嘌呤和8-氧代鸟嘌呤。我们现在报告，迄今尚未确定的第三种核酸修饰的基本部分，即RNA中的RX1和DNA中的DX1，是2-肼基次黄嘌呤（N2-氨基鸟嘌呤）。2-Hyrazrazinoinosine和2-hydrazinodeoxyinosine，是通过采用已公开的程序合成的，分别用2-硝基丙烷处理的大鼠的肝RNA和DNA的RX1和DX1进行共色谱。2-Hyrazrazinoinosine和2-hydrazinodeoxyinosine在溶液中像体内产物RX1和DX1一样不稳定。在中性pH下，次黄嘌呤核苷是分解的主要产物，而在pH等于或大

  DOI：

  10.1021/tx980160c

文献信息

• Synthesis, Properties, and Pharmacokinetic Studies of N2-Phenylguanine Derivatives as Inhibitors of Herpes Simplex Virus Thymidine Kinases
  作者：Hongyan Xu、Giovanni Maga、Federico Focher、Emil R. Smith、Silvio Spadari、Joseph Gambino、George E. Wright

  DOI：10.1021/jm00001a010

  日期：1995.1

  Two series of selective inhibitors of herpes simplex virus types 1 and 2 (HSV1,2) thymidine kinases (TK) have been developed as potential treatment of recurrent virus infections. Among compounds related to the potent base analog N-2-[m-(trifluoromethyl)phenyl]guanine (mCF(3)PG), none was a more potent inhibitor than mCF(3)PG itself. Compounds related to the nucleoside N-2-phenyl-2'-deoxyguanosine (PhdG), but with alkyl, hydroxyalkyl, and related substituents at the 9-position in place of the glycosyl group of PhdG, retained significant but variable inhibitory potencies against the HSV TKs. The most potent inhibitor of HSV1 TK among 9-substituted derivatives, 9-(4-hydroxybutyl)-N-2-phenylguanine (HBPG), was a competitive inhibitor with respect to the substrate thymidine but was not itself a substrate for the enzyme. Water solubilities and 1-octanol:water partition coefficients for the 9-substituted N-2-phenylguanines were linearly but oppositely related to the sum of hydrophobic fragmental constants (Sigma f) of the 9-substituents. Four of the inhibitors were given as solutions to mice by iv and ip routes, and the time course of their plasma concentrations was determined by HPLC analysis of the parent compounds. HBPG was completely absorbed by the ip route, and the plasma concentration could be prolonged by use of suspension formulations. HBPG is a candidate for animal trials of the ability of TK inhibitors to prevent recurrent herpes virus infections.
• Structure-activity relationships of N2-substituted guanines as inhibitors of HSV1 and HSV2 thymidine kinases
  作者：Catherine Hildebrand、Daniele Sandoli、Federico Focher、Joseph Gambino、Giovanni Ciarrocchi、Silvio Spadari、George Wright

  DOI：10.1021/jm00163a033

  日期：1990.1

  A series of N2-phenylguanines was synthesized and tested for inhibition of the thymidine kinases encoded by Herpes simplex viruses type 1 and type 2. Compounds with hydrophobic, electron-attracting groups in the meta position of the phenyl ring such as m-trifluoromethyl (m-CF3PG, IC50 = 0.1 microM) were the most potent inhibitors of both enzymes. Many derivatives were significantly more potent against the type 2 thymidine kinase, and can effectively discriminate between the two enzymes. Among other N2-substituted guanines, alkyl and benzyl derivatives were moderately potent inhibitors, and the type 2 enzyme was again more sensitive than the type 1 enzyme. None of the compounds inhibited the thymidine kinase isolated from the host HeLa cell line, suggesting that members of this class of compounds may be useful nonsubstrate, antiviral compounds for latent herpesvirus infections.
• HILDEBRAND, CATHERINE;SANDOLI, DANIELE;FOCHER, FEDERICO;GAMBINO, JOSEPH;C+, J. MED. CHEM., 33,(1990) N, C. 203-206
  作者：HILDEBRAND, CATHERINE、SANDOLI, DANIELE、FOCHER, FEDERICO、GAMBINO, JOSEPH、C+

  DOI：——

  日期：——
• US5646155A
  申请人：——

  公开号：US5646155A

  公开（公告）日：1997-07-08
• US6355785B1
  申请人：——

  公开号：US6355785B1

  公开（公告）日：2002-03-12