2',3'-isopropylideneadenosine | 362-75-4

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷中间体
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-isopropylideneadenosine
• 英文别名: 2',3'-Isopropyliden-β-DL-adenosin；[(3aS,4S,6S,6aS)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 362-75-4
• 化学式: C₁₃H₁₇N₅O₄
• 分子量: 307.309
• InChiKey: LCCLUOXEZAHUNS-GTBBIVDNSA-N

物化性质

• 熔点：
  221-222 °C(lit.)
• 沸点：
  447.81°C (rough estimate)
• 密度：
  1.2370 (rough estimate)
• 溶解度：
  可溶于二恶烷（轻微，超声处理）、DMSO（轻微）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

制备方法与用途

应用

2',3'-异丙叉腺苷是一种白色至类白色的粉末或结晶，可用作生化试剂。

反应信息

• 作为反应物：
  描述：

  2',3'-isopropylideneadenosine 在 二氯乙酸 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 吡啶 、 盐酸羟胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 以80%的产率得到L-2',3'-O-isopropylideneadenosine-5'-carboxaldehyde oxime
  参考文献：
  名称：

  L-腺苷及其衍生物是S-腺苷-L-高半胱氨酸水解酶的底物吗？

  摘要：

  2'，3'-O-异亚丙基-L-腺苷的Moffatt氧化，用羟胺处理所得的粗制5'-醛，然后脱保护，得到L-腺苷5'-甲醛醛肟，已知其对映异构体是强力抑制剂S-腺苷-L-高半胱氨酸（AdoHcy）水解酶。发现L-腺苷及其5'-醛肟衍生物作为AdoHcy水解酶的抑制剂是无活性的。对接计算显示，与D-Ado相比，L-腺苷与AdoHcy水解酶的结合更弱（能量更高），特异性更低（簇数更多）。

  DOI：

  10.1021/jm0490484
• 作为产物：
  描述：

  在 Pd-BaSO₄ ammonium hydroxide 、 sodium tetrahydroborate 、 水 、 氢气 、 4-甲基苯磺酸吡啶 、 1-羟基苯并三唑 、 邻硝基苯磺酰氯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 丙酮 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~35.0 ℃ 、101.33 kPa 条件下， 生成 2',3'-isopropylideneadenosine
  参考文献：
  名称：

  From Furan to Nucleosides

  摘要：

  DOI：

  10.1021/ja9537336

文献信息

• Design and synthesis of Coenzyme A analogues as Aurora kinase A inhibitors: An exploration of the roles of the pyrophosphate and pantetheine moieties
  作者：Fiona Bellany、Yugo Tsuchiya、Trang M. Tran、A.W. Edith Chan、Helen Allan、Ivan Gout、Alethea B. Tabor

  DOI：10.1016/j.bmc.2020.115740

  日期：2020.11

  Coenzyme A (CoA) is a highly selective inhibitor of the mitotic regulatory enzyme Aurora A kinase, with a novel mode of action. Herein we report the design and synthesis of analogues of CoA as inhibitors of Aurora A kinase. We have designed and synthesised modified CoA structures as potential inhibitors, combining dicarbonyl mimics of the pyrophosphate group with a conserved adenosine headgroup and

  辅酶A（CoA）是有丝分裂调节酶Aurora A激酶的高度选择性抑制剂，具有新颖的作用方式。在本文中，我们报道了作为Aurora A激酶抑制剂的CoA类似物的设计和合成。我们已经设计并合成了修饰的CoA结构作为潜在的抑制剂，将焦磷酸酯基团的二羰基模拟物与保守的腺苷头基和不同长度的基于泛神碱的尾基结合起来。泛酸尾部末端带有-SH基团的类似物显示出最佳的IC50，这可能是由于与Aurora A激酶Cys290共价键形成所致。
• NAD-based inhibitors with anticancer potential
  作者：Krzysztof Felczak、Robert Vince、Krzysztof W. Pankiewicz

  DOI：10.1016/j.bmcl.2013.11.005

  日期：2014.1

  Three classes of novel inhibitors of inosine monophosphate dehydrogenase have been prepared and their anti-proliferative properties were evaluated against several cancer cell lines.(1) Mycophenolic adenine dinucleotide analogues (8-13) containing a substituent at the C2 of adenine ring were found to be potent inhibitors of IMPDH (K-i's in range of 0.6-82 nM) and sub-mu M inhibitors of leukemic K562 cell proliferation. (2) Mycophenolic adenosine (D and L) esters (20 and 21) showed a potent inhibition of IMPDH2 (K-i = 102 and K-i = 231 nM, respectively) and inhibition of K562 cell growth (IC50 = 0.5 and IC50 = 1.6 mu M). These compounds serve both as inhibitors of the enzyme and as a depot form of mycophenolic acid. The corresponding amide analogue 22, also a potent inhibitor of IMPDH (K-i = 84 nM), did not inhibit cancer cell proliferation. (3) Mycophenolic-(L)-and (D)-valine adenine diamide derivatives 25 (K-i = 9 nM) and 28 (K-i = 3 nM) were found to be very potent enzymatically, but did not inhibit proliferation of cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and biological activities of 5′-ethylenic and acetylenic modified l-nucleosides and isonucleosides
  作者：Jun-Feng Wang、Xiao-Da Yang、Liang-Ren Zhang、Zhen-Jun Yang、Li-He Zhang

  DOI：10.1016/j.tet.2004.06.131

  日期：2004.9

  Two series of 6'-halovinyl-adenosine stereoisomers including 5'-ethylenic and acetylenic substituted L-adenosine, 5'-ethylenic and acetylenic substituted isonucleosides were synthesized. In the L-nucleoside series, compounds 6b, 8b, 10b and 13b showed modest inhibition of SAH hydrolase (21, 44, 50 and 26% respectively) at 100 muM. The L-isomers of 5'-ethylenic and acetylenic modified isonucleoside 23, 24 exhibited no activity for the inhibition of SAH hydrolase, however, the D-isomers 30 and 31 showed some activities in the same test (35 and 21%). It indicated clearly the strict stereochemical requirement for the substrate of SAH hydrolase. Compounds 6b, 8b, 8c, 11b exhibited modest to good inhibition effects on the growth of HeLa cells or Bel-7420 cells at 1 muM (64, 44, 53 and 82% respectively). (C) 2004 Elsevier Ltd. All rights reserved.
• Angle, Steven R.; Yang, Wenjin, Journal of the American Chemical Society, 1990, vol. 112, # 11, p. 4524 - 4528
  作者：Angle, Steven R.、Yang, Wenjin

  DOI：——

  日期：——
• From Furan to Nucleosides
  作者：Barry M. Trost、Zhongping Shi

  DOI：10.1021/ja9537336

  日期：1996.1.1