6-N-羟氨基嘌呤 | 5667-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-N-羟氨基嘌呤
• 英文名称: N-(7(9)H-purin-6-yl)-hydroxylamine
• 英文别名: N-(7(9)H-Purin-6-yl)-hydroxylamin；N-hydroxy-1H-adenine；6-N-Hydroxylaminopurine；N-(7H-purin-6-yl)hydroxylamine
• CAS: 5667-20-9
• 化学式: C₅H₅N₅O
• 分子量: 151.128
• InChiKey: CBCQWVQNMGNYEO-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C (decomp)
• 沸点：
  273.11°C (rough estimate)
• 密度：
  1.4456 (rough estimate)
• 溶解度：
  可溶于酸性水溶液（少许）、DMSO（少许）
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P280,P305+P351+P338,P308+P313
• 危险品运输编号：
  2811
• 危险性描述：
  H315,H319,H335,H360
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  腺嘌呤	adenine	73-24-5	C5H5N5	135.128

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  腺嘌呤	adenine	73-24-5	C5H5N5	135.128

反应信息

• 作为反应物：
  描述：

  6-N-羟氨基嘌呤 在 alkaline Na₂S₂O₄ 作用下， 生成 腺嘌呤
  参考文献：
  名称：

  Synthesis and Properties of Some 6-Substituted Purines¹

  摘要：

  DOI：

  10.1021/ja01548a033
• 作为产物：
  描述：

  腺嘌呤 生成 6-N-羟氨基嘌呤
  参考文献：
  名称：

  CLEMENT, B.;KUNZE, TH., ARCH. PHARM., 321,(1988) N 9, C. 601

  摘要：

  DOI：

文献信息

• Nitrosopurines En Route to Potently Cytotoxic Asmarines
  作者：Kanny K. Wan、Kotaro Iwasaki、Jeffrey C. Umotoy、Dennis W. Wolan、Ryan A. Shenvi

  DOI：10.1002/anie.201411493

  日期：2015.2.16

  A nitrosopurine ene reaction easily assembles the asmarine pharmacophore and transmits remote stereochemistry to the diazepine‐purine hetereocycle. This reaction generates potent cytotoxins which exceed the potency of asmarine A (1.2 μM IC50) and supersede the metabolites as useful leads for biological discovery.

  亚硝基嘌呤烯的反应可以很容易地组装出海蓝宝石药效团并将远程立体化学传递给二氮杂嘌呤-嘌呤杂环。该反应生成超过asmarine A的（1.2μ的效力强效的细胞毒素中号IC 50）和取代的代谢物作为生物发现有用线索。
• Structure−Activity Relationships of Adenine and Deazaadenine Derivatives as Ligands for Adenine Receptors, a New Purinergic Receptor Family
  作者：Thomas Borrmann、Aliaa Abdelrahman、Rosaria Volpini、Catia Lambertucci、Edgars Alksnis、Simone Gorzalka、Melanie Knospe、Anke C. Schiedel、Gloria Cristalli、Christa E. Müller

  DOI：10.1021/jm9006356

  日期：2009.10.8

  Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure−activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position

  合成并研究了在[ 3]中带有2-，N 6-，7-，8和/或9位取代基的腺嘌呤衍生物和一系列脱氮嘌呤。H]腺嘌呤在大鼠大脑皮层膜制剂（rAde1R）中对腺嘌呤受体的结合研究。观察到陡峭的结构-活性关系。最好的取代是在8位（氨基，二甲基氨基，哌啶基，哌嗪基）或9位（2-吗啉代乙基）中带有碱性残基或在6位氨基官能团处引入极性取代基（羟基，氨基，乙酰基）是最好的修改。在稳定表达rAde1R的1321N1星形细胞瘤细胞的腺苷酸环化酶测定中，对所选腺嘌呤衍生物的功能评估表明，所研究的所有化合物均为激动剂或部分激动剂。在人类胚胎肾脏（HEK293）细胞的结合研究中还对化合物的子集进行了研究，该细胞还表达了高亲和力的腺嘌呤结合位点。人细胞系的结构亲和力关系与rAde1R相似，但不完全相同。特别是，N 6-乙酰腺嘌呤（25，K i大鼠：2.85μM; K i人：0.515μM）和8-氨基腺嘌呤（33，K i
• WO2007/135380
  申请人：——

  公开号：——

  公开（公告）日：——
• The Mitochondrial Amidoxime Reducing Component (mARC) Is Involved in Detoxification of N-Hydroxylated Base Analogues
  作者：Nina Krompholz、Carmen Krischkowski、Debora Reichmann、Dieter Garbe-Schönberg、Ralf-R. Mendel、Florian Bittner、Bernd Clement、Antje Havemeyer

  DOI：10.1021/tx300298m

  日期：2012.11.19

  The "mitochondrial Amidoxime Reducing Component" (mARC) is the newly discovered fourth molybdenum enzyme in mammals. All hitherto analyzed mammals express two mARC proteins, referred to as mARC1 and mARC2. Together with their electron transport proteins cytochrome b(5) and NADH cytochrome b(5) reductase, they form a three-component enzyme system and catalyze the reduction of N-hydroxylated prodrugs. Here, we demonstrate the reductive detoxification of toxic and mutagenic N-hydroxylated nucleobases and their corresponding nucleosides by the mammalian mARC-containing enzyme system. The N-reductive activity was found in all tested tissues with the highest detectable conversion rates in liver, kidney, thyroid, and pancreas. According to the presumed localization, the N-reductive activity is most pronounced in enriched mitochondrial fractions. In vitro assays with the respective recombinant three-component enzyme system show that both mARC isoforms are able to reduce N-hydroxylated base analogues, with mARC1 representing the more efficient isoform. On the basis of the high specific activities with N-hydroxylated base analogues relative to other N-hydroxylated substrates, our data suggest that mARC proteins might be involved in protecting cellular DNA from misincorporation of toxic N-hydroxylated base analogues during replication by converting them to the correct purine or pyrimidine bases, respectively.
• Anti-malarial activity of N6-modified purine analogues
  作者：Kathleen Too、Daniel M. Brown、Emily Bongard、Vanessa Yardley、Livia Vivas、David Loakes

  DOI：10.1016/j.bmc.2007.05.038

  日期：2007.8

  Plasmodium falciparum causes one of the deadliest forms of malaria and resistance to the currently available drugs makes it imperative to develop new, safe and potent drugs. Parasites such as P. falciparum are unable to synthesise purines de novo and to this end often have multiple purine uptake and salvage systems. With this in mind, we have designed and synthesised libraries of purine analogues as potential anti-malarial agents. Herein, we report three compounds with promising activity against the highly chloroquine-resistant VS1 P. falciparum namely: N-6-hydroxyadenine (1c), 2-amino-N-6-aminoadenosine (2b) and 2-amino-N-6-amino-N-6-methyladenosine (4b). (c) 2007 Elsevier Ltd. All rights reserved.