腺苷酸-5-羧酸 | 3415-09-6

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 腺苷酸-5-羧酸
• 中文别名: 无
• 英文名称: adenosine 5'-carboxylic acid
• 英文别名: 5′-carboxyadenosine；5'-Carboxyladenosine；5'-carboxyadenosine；5'-oxyadenosine；1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid；9-Riburonosyladenine；(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylic acid
• CAS: 3415-09-6
• 化学式: C₁₀H₁₁N₅O₅
• mdl: MFCD00057014
• 分子量: 281.228
• InChiKey: IBYWUFHJUDTSOC-SOVPELCUSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  756.3±70.0 °C(Predicted)
• 密度：
  2.24±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、水

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  腺苷酸-5-羧酸 在 氯化亚砜 作用下， 反应 18.0h， 生成 5-N-乙基酰胺基腺苷
  参考文献：
  名称：

  N6-Substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors

  摘要：

  The coronary vasoactivity of N-ethyl-1'-deoxy-1'-(6-amino-9H-purin-9-yl)-beta-D-ribofuranuronamide (NECA, 1) is over 2 orders of magnitude greater than that of adenosine, and the vasoactivity of certain N6-substituted adenosines is as much as 1 order of magnitude greater. Such results suggest that a combination of appropriate modifications at N6 and C-5' might additively augment the agonist potency of adenosine. At low temperatures 1-deoxy-1-(6-chloro-9H-purin-9-yl)-2',3'-O-isopropylidene- beta-D-ribofuranosyl chloride (5), obtained in three steps from inosine, reacts with amines to yield uronamides. The subsequent reaction of such uronamides with amines at elevated temperatures displaces the purine 6-chloro group to yield, after deblocking, N-alkyl(or aryl)-N6-alk(ar)yl-adenosine-5'-uronamides. At the coronary artery A2 receptor the potency of N6-modified analogues of 1 is similar to that of the N6-substituted adenosine, rather than equal to or greater than 1. As agonists in the A2 receptor-mediated stimulation of adenylate cyclase in plasma membranes of PC12 pheochromocytoma cells or human platelets, N6-substituted analogues of 1 are intermediate between the high potency of 1 and the lower potency of the N6-substituted adenosines. At the A1 receptor of rat brain the potency of an N6-substituted analogue of 1 is often greater than that of the corresponding N6-substituted adenosine. At all four receptors, replacing the ethyl group of N-ethyl-N6-3-pentyladenosine-5'-uronamide by larger alkyl groups reduces potency; amides of secondary amines are inactive or have only marginal activity. Analogues of 1 containing a chiral center in the N6 substituent retain the stereoselectivity characteristic of each of the four receptors. Thus, at either A1 or A2 adenosine receptors, adenosine analogues interact with both the N6 and the C-5' receptor regions. However, the effects of N6 and C-5' modifications on potency are less than additive, evidence that the interaction of a substituent with its receptor region influences the interaction of other substituents with their respective receptor regions.

  DOI：

  10.1021/jm00159a020
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 甲酸 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 46.0h， 生成 腺苷酸-5-羧酸
  参考文献：
  名称：

  用于检测衍生自ω-6多不饱和脂肪酸的特定环状DNA加合物的单克隆抗体

  摘要：

  多不饱和脂肪酸（PUFA）的脂质过氧化作用是α，β-不饱和醛的内源性来源，可与DNA反应生成各种环状加合物。致突变的环状加合物，特别是衍生自ω-6PUFA氧化的那些，可能有助于促进与ω-6PUFA相关的癌症活性。（E）-4-羟基-2-壬烯醛（HNE）是ω-6PUFAs氧化的独特产物。HNE与脱氧鸟苷（dG）反应产生诱变的1，N 2-丙去氧鸟苷加合物（HNE-dG）。较早的研究表明，HNE也可以被氧化成其环氧化物（EH），并且EH可以与脱氧腺苷（dA）反应，形成经过充分研究的εdA和取代的乙炔加合物。使用基于液相色谱的串联质谱（LC-MS / MS）方法，我们先前报道了EH衍生的7-（1'，2'-二羟基庚基）-1，N 6的检测-enodenodeoxyadenosine（DHHεdA）作为啮齿动物和人体组织中DNA的新型内源性背景加合物。DHHεdA的形成，修复和诱变及其在细胞中的生物学后果

  DOI：

  10.1021/acs.chemrestox.8b00111

文献信息

• 一种用于修复角膜损伤的METTL3抑制剂及其药物应用
  申请人：高颜苑科技（深圳）有限责任公司

  公开号：CN114057742A

  公开（公告）日：2022-02-18

  本发明公开了一种用于修复角膜损伤的METTL3抑制剂及其药物应用，该METTL3抑制剂是通式(I)所示的化合物或其互变异构体、内消旋体、外消旋体、对映异构体和非对映异构体，或其混合物或其可药用的盐。本发明METTL3抑制剂用于修复角膜损伤。本发明提供一种能够抑制METTL3蛋白活性从而起到修复角膜损伤的小分子化合物及其药物应用，具体为以METTL3蛋白结构为基础的有机小分子及相关药物的应用。本发明公开的化合物是一种有效的METTL3抑制剂，该化合物能够很好的抑制m6A修饰的生成。通过本发明中的实验可以得出，本发明中公开的化合物可以通过抑制METTL3蛋白质从而起到很好的角膜修复效果。
• Synthesis and antiviral activities of new acyclic and “double-headed” nucleoside analogues
  作者：Xinying Zhang、Adel Amer、Xuesen Fan、Jan Balzarini、Johan Neyts、Erik De Clercq、Mark Prichard、Earl Kern、Paul F. Torrence

  DOI：10.1016/j.bioorg.2006.11.003

  日期：2007.6

  inhibition of orthopoxviruses by nucleoside analogues, a variety of novel chemical entities were synthesized. These included a series of pyrimidine 5-hypermodified acyclic nucleoside analogues based upon recently discovered new leads, and some previously unknown "double-headed" or "abbreviated" nucleosides. None of the synthetic products possessed significant activity against two representative orthopoxviruses;

  为了发展对核苷类似物抑制正痘病毒的构效关系的认识，合成了多种新颖的化学实体。这些包括基于最近发现的新先导的一系列嘧啶5-超修饰的无环核苷类似物，以及一些以前未知的“双头”或“缩写”核苷。没有一种合成产物对两种代表性的正痘病毒具有显着的活性。即牛痘病毒和牛痘病毒。它们还没有针对一系列其他DNA和RNA病毒的显着活性。就正痘病毒和疱疹病毒的结果而言，该结果可能表明核苷类似物5'-磷酸化具有抗病毒功效的必要性。
• Ruthenium tetraoxide: a mild reagent for the oxidation of 2′,3′-O-isopropylidene purine nucleosides
  作者：Ambarish K. Singh、Rajender S. Varma

  DOI：10.1016/s0040-4039(00)74197-9

  日期：1992.4

  2′,3′-O-isopropylidene purine nucleosides have been oxidized with ruthenium tetraoxide to provide the corresponding 5′-carboxylic acids in quantitative yields under neutral conditions.

  2'，3'-O-异亚丙基嘌呤核苷已被四氧化钌氧化，在中性条件下以定量收率提供了相应的5'-羧酸。
• Biomarkers for Carcinogenesis and Uses Thereof
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20190227072A1

  公开（公告）日：2019-07-25

  Provided herein are methods of reducing the recurrence of liver cancer in a subject.

  本文提供了一种减少受试者肝癌复发的方法。
• PHOTOLUMINESCENT MOLECULAR COMPLEX AND METHOD FOR DETERMINING OF THE CONCENTRATION OF SAID MOLECULAR COMPLEX
  申请人：Uri Asko

  公开号：US20140057284A1

  公开（公告）日：2014-02-27

  The invention concerns novel molecular complexes with photoluminescent probes whose specific association with purine-binding proteins leads to increased emission of long lifetime luminescence, and the application of the probes for monitoring activity of protein kinases (PKs) and other purine-binding proteins, screening of compounds as inhibitors of PKs and characterization of inhibitors targeted to the kinase, and methods of manufacturing of such probes. The invention concerns also the use of the improved method for monitoring activity of protein kinases in living cells, characterization of inhibitors of protein kinases, analysis of protein kinase-based disease biomarkers and other tasks of biological and medical importance.

  本发明涉及新型分子复合物，其中包含光致发光探针，其与嘌呤结合蛋白的特定结合导致发射长寿命荧光的增加，以及探针在监测蛋白激酶（PKs）和其他嘌呤结合蛋白的活性、筛选PKs抑制剂化合物和定向于激酶的抑制剂的表征以及制造这种探针的方法。本发明还涉及改进的方法用于监测活细胞中的蛋白激酶活性，表征蛋白激酶抑制剂，分析基于蛋白激酶的疾病生物标志物和其他生物和医学重要任务的使用。