8-bromoinosine 5'-monophosphate | 75204-33-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 8-bromoinosine 5'-monophosphate
• 英文别名: 8-bromoinosine 5'-phosphate；8-Bromoinosine 5'-(dihydrogen phosphate)；[(2R,3S,4R,5R)-5-(8-bromo-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 75204-33-0
• 化学式: C₁₀H₁₂BrN₄O₈P
• 分子量: 427.105
• InChiKey: DAKIWOGVDCFLAA-UUOKFMHZSA-N

物化性质

• 密度：
  2.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  8-bromoadenosine-5'-monophosphate 在 sodium hydroxide 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 生成 8-bromoinosine 5'-monophosphate
  参考文献：
  名称：

  Inhibition of inosinic acid dehydrogenase by 8-substituted purine nucleotides

  摘要：

  A series of 8-substituted derivatives of adenosine monophosphate (AMP) and inosine monophosphate (IMP) were synthesized and examined for their ability to inhibit Escherichia coli IMP dehydrogenase. All compounds studied were competitive inhibitors in IMP-dependent competition studies and lacked substrate activity. In oxidized nicotinamide adenine dinucleotide dependent studies, 8-(p-NO2PhCH2S)-IMP was noncompetitive and 8-(p-NO2PhCH2S)-AMP showed mixed inhibition. Multiple regression analysis showed that for the series of 8-(para-substituted-benzylthio)-AMPs and -IMPs, the electron-withdrawing ability of the para substituent on the benzylthio moiety correlated best with log Ki of the analogues.

  DOI：

  10.1021/jm00142a007

文献信息

• A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs)
  作者：Alice Collier、Gerd Wagner

  DOI：10.1039/b614477b

  日期：——

  We report a simple and high-yielding two-step procedure for the preparation of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). The key step of our synthesis is the Suzuki–Miyaura coupling of unprotected 8-bromo GMP and 8-bromo GTP with various arylboronic acids in aqueous solution. The 8-bromoguanosine 5′-phosphates required as cross-coupling substrates were prepared from 8-bromoguanosine via an optimised Yoshikawa procedure.

  我们报告了一种简单而高产的两步法制备 8-芳基鸟苷酸单磷酸和三磷酸酯（8-芳基 GXP）。我们合成的关键步骤是在水溶液中将未受保护的 8-溴 GMP 和 8-溴 GTP 与各种芳基硼酸进行铃木-宫脲偶联。作为交叉耦合底物所需的 8-溴鸟苷 5′-磷酸酯是通过优化吉川程序从 8-溴鸟苷制备的。
• Therapeutics
  申请人：——

  公开号：US20040214789A1

  公开（公告）日：2004-10-28

  The use of a compound of formula (Ia): 1 wherein A and B are independently selected from a cyclic ring, wherein each of which cyclic rings A and B may be optionally substituted at at least one ring position; and L is a suitable linker; or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for use in inhibiting ADP-ribosyl cyclase.

  使用式(Ia)的化合物制造药物，其中式(Ia)如下：1其中A和B独立地选择自一个环状环，其中环状环A和B中的每一个都可以在至少一个环位被可选地取代；且L是适当的连接基；或其药学上可接受的盐。该药物用于抑制ADP核糖环化酶。
• Rapid Synthetic Route toward Structurally Modified Derivatives of Cyclic Adenosine 5‘-Diphosphate Ribose
  作者：Gerd K. Wagner、Andreas H. Guse、Barry V. L. Potter

  DOI：10.1021/jo050085s

  日期：2005.6.1

  A concise synthesis of five new analogues of the second messenger cADPR (cyclic adenosine 5'-diphosphate ribose) is presented. The synthetic plan centered around the key derivative 8-Br-N1-cIDPR (cyclic 8-Br-inosine 5'-diphosphate ribose, 2), which was prepared in only three steps from IMP (inosine 5'-monophosphate) via an unusual enzymatic cyclization reaction. The enhanced stability of 2 allowed for the direct modification of this cyclic dinucleotide at the 8 position, providing the unsubstituted parent N1-cIDPR (4) as well as the 8-phenyl (5), 8-azido (6), and 8-amino (7) N1-cIDPR analogues. In Jurkat T-lymphocytes, N1-cIDPR 4 induced Ca2+ release with an almost identical profile as the natural agonist cADPR, illustrating the value of this approach.
• THERAPEUTIC COMPOSITIONS FOR MODULATING THE IMMUNE RESPONSE IN A MAMMAL AND USE THEREOF
  申请人：UNIVERSITY OF BATH

  公开号：EP1395267A2

  公开（公告）日：2004-03-10
• [EN] THERAPEUTICS<br/>[FR] AGENTS THERAPEUTIQUES
  申请人：UNIV BATH

  公开号：WO2002098397A2

  公开（公告）日：2002-12-12

  The use of a compound of formula (Ia): wherein A and B are independently selected from a cyclic ring, wherein each of which cyclic rings A and B may be optionally substituted at least one ring position; and L is a suitable linker; or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for use in inhibiting ADP-ribosyl cyclase.