9-(2-bromoethyl)-2,6-diamino-9H-purine | 150899-81-3

• 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: 9-(2-bromoethyl)-2,6-diamino-9H-purine
• 英文别名: 9-(2-bromoethyl)-2,6-diaminopurine；9-(2-Bromoethyl)purine-2,6-diamine
• CAS: 150899-81-3
• 化学式: C₇H₉BrN₆
• 分子量: 257.093
• InChiKey: RBECBEDTGHITGS-UHFFFAOYSA-N

物化性质

• 沸点：
  563.9±60.0 °C(Predicted)
• 密度：
  2.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(2-bromoethyl)-2,6-diamino-9H-purine 生成 Ethanethioic acid, S-[[2,6-diamino-9H-purine-9-yl]ethyl]ester
  参考文献：
  名称：

  Macrolides with antibacterial activity

  摘要：

  该发明提供了具有改进生物性能和改进稳定性的新大环内酯类抗生素的公式(I)：其中R1为氢、氰基、—S(L)mR2、—S(O)(L)mR2或—S(O)2(L)mR2；L代表—(CH2)n—或—(CH2)nZ(CH2)n′—；m为0或1；n为1、2、3或4；n′为0、1、2、3或4；Z为O、S或NH；R2为氢、烷基、杂环烷基或芳基；其中杂环烷基和芳基基团可能进一步取代；*表示手性中心，为(R)或(S)形式，以及其药学上可接受的酸盐或体内可水解酯。

  公开号：

  US20030199459A1
• 作为产物：
  描述：

  2,6-二氨基嘌呤硫酸盐 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以63%的产率得到9-(2-bromoethyl)-2,6-diamino-9H-purine
  参考文献：
  名称：

  A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency

  摘要：

  A series of tailor-made molecules, 1 and 4-7, have been prepared to recognize and cleave DNA at apurinic sites. These molecules incorporate in their structure different units designed for specific functions: (1) an intercalator for DNA binding, (2) a nucleic base for abasic site recognition, and (3) a linker endowed with both a binding function and a cleavage function (Scheme II). The constituent units were varied successively in the series of molecules to get insight into their mode of action and prepare more active compounds. H-1 NMR spectroscopy reveals the absence of intramolecular ring-ring stacking interactions in water between the base and the intercalator in all molecules 1 and 4-7. All bind to calf thymus DNA with binding constants ranging from 10(4) to 10(6) M-1. Their nuclease activity was estimated by measuring their ability to induce single strand breaks in depurinated pBR 322 plasmid DNA. The most efficient molecule, 5, exhibits high recognition selectivity and cleavage efficiency: at nanomolar concentrations, 5 recognizes and cleaves the abasic lesion present in a DNA molecule containing an average of 1.8 apurinic sites in its 4 362 base pairs sequence. Molecule 5 exhibits higher cleaving efficiency than the reported tripeptide Lys-Trp-Lys: 10(-8) M concentrations of the former (5) lead to cleavage ratios comparable to those observed for the latter used as 10(-3) M concentration. This enzyme mimic 5 can be used advantageously as a substitute to the natural nuclease for in vitro cleavage of depurinated DNA.

  DOI：

  10.1021/ja00075a011

文献信息

• Potentiation of BCNU Cytotoxicity by Molecules Targeting Abasic Lesions in DNA
  作者：Karine Alarcon、Martine Demeunynck、Jean Lhomme、Danièle Carrez、Alain Croisy

  DOI：10.1016/s0968-0896(01)00097-9

  日期：2001.7

  We describe the synthesis, DNA binding measurements and pharmacological properties of a series of new heterodimeric molecules, in which a 2,6-diaminopurine is linked to a 9-aminoacridine chromophore. The linking chain contains a central N,N'-disubstituted guanidine, connected to the two chromophores by polymethylenic units of variable length. (C) 2001 Elsevier Science Ltd. All rights reserved.
• NEW MACROLIDES WITH ANTIBACTERIAL ACTIVITY
  申请人：Basilea Pharmaceutica AG

  公开号：EP1313751B1

  公开（公告）日：2008-09-17
• US6740642B2
  申请人：——

  公开号：US6740642B2

  公开（公告）日：2004-05-25
• Macrolides with antibacterial activity
  申请人：——

  公开号：US20030199459A1

  公开（公告）日：2003-10-23

  The invention provides new macrolides antibiotics of formula (I) with improved biological properties and improved stability formula (I): wherein R 1 is hydrogen, cyano, —S(L) m R 2 , —S(O)(L) m R 2 , or —S(O) 2 (L) m R 2 ; L represents —(CH 2 ) n — or —(CH 2 ) n Z(CH 2 ) n′ —-; m is 0 or 1; n is 1, 2, 3, or 4; n′ is 0, 1, 2, 3, or 4; Z is O, S or NH; R2 is hydrogen, alkyl, heterocyclyl or aryl; which heterocyclyl and the aryl groups may be further substituted; * indicates a chiral center which is in the (R) or (S) form and pharmaceutically acceptable acid addition salts or in vivo cleavable esters thereof. 1

  该发明提供了具有改进生物性能和改进稳定性的新大环内酯类抗生素的公式(I)：其中R1为氢、氰基、—S(L)mR2、—S(O)(L)mR2或—S(O)2(L)mR2；L代表—(CH2)n—或—(CH2)nZ(CH2)n′—；m为0或1；n为1、2、3或4；n′为0、1、2、3或4；Z为O、S或NH；R2为氢、烷基、杂环烷基或芳基；其中杂环烷基和芳基基团可能进一步取代；*表示手性中心，为(R)或(S)形式，以及其药学上可接受的酸盐或体内可水解酯。
• A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency
  作者：Abdellatif Fkyerat、Martine Demeunynck、Jean Francois Constant、Pierre Michon、Jean Lhomme

  DOI：10.1021/ja00075a011

  日期：1993.11

  A series of tailor-made molecules, 1 and 4-7, have been prepared to recognize and cleave DNA at apurinic sites. These molecules incorporate in their structure different units designed for specific functions: (1) an intercalator for DNA binding, (2) a nucleic base for abasic site recognition, and (3) a linker endowed with both a binding function and a cleavage function (Scheme II). The constituent units were varied successively in the series of molecules to get insight into their mode of action and prepare more active compounds. H-1 NMR spectroscopy reveals the absence of intramolecular ring-ring stacking interactions in water between the base and the intercalator in all molecules 1 and 4-7. All bind to calf thymus DNA with binding constants ranging from 10(4) to 10(6) M-1. Their nuclease activity was estimated by measuring their ability to induce single strand breaks in depurinated pBR 322 plasmid DNA. The most efficient molecule, 5, exhibits high recognition selectivity and cleavage efficiency: at nanomolar concentrations, 5 recognizes and cleaves the abasic lesion present in a DNA molecule containing an average of 1.8 apurinic sites in its 4 362 base pairs sequence. Molecule 5 exhibits higher cleaving efficiency than the reported tripeptide Lys-Trp-Lys: 10(-8) M concentrations of the former (5) lead to cleavage ratios comparable to those observed for the latter used as 10(-3) M concentration. This enzyme mimic 5 can be used advantageously as a substitute to the natural nuclease for in vitro cleavage of depurinated DNA.