(9ci)-5-氨基-1-甲基-1H-咪唑-4-羧酰胺 | 21343-04-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (9ci)-5-氨基-1-甲基-1H-咪唑-4-羧酰胺
• 中文别名: 5-氨基-1-甲基-1H-咪唑-4-羧酰胺；1-甲基-4-酰胺基-5-氨基咪唑；5-氨基-1-甲基-1H-咪唑-4-甲酰胺
• 英文名称: 5-amino-1-methyl-1H-imidazole-4-carboxamide
• 英文别名: 5-amino-1-methylimidazole-4-carboxamide
• CAS: 21343-04-4
• 化学式: C₅H₈N₄O
• mdl: MFCD14281882
• 分子量: 140.145
• InChiKey: UZHKJZZQGXMAKP-UHFFFAOYSA-N

物化性质

• 熔点：
  254 °C (decomp)
• 沸点：
  440.4±25.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  (9ci)-5-氨基-1-甲基-1H-咪唑-4-羧酰胺 在 tetraphosphorus decasulfide 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以69.4%的产率得到5-氨基-1-甲基咪唑-4-硫代甲酰胺
  参考文献：
  名称：

  Analogs of AICA- and IsoAICA Ribosides and Their Methylated Base Counterparts

  摘要：

  A mild, convenient and efficient synthesis has been developed for imidazole-4-thiocarboxamide and imidazole-5-thiocarboxamide ribosides and the analogous selenocarboxamides. This methodology, i.e., DMF saturated with H2S or H2Se, also converts the corresponding N-methylated bases to the corresponding amides. The imidazole-4(5)-selenocarboxamides were shown to be sensitive to base (pH 11) and were easily converted back to their cyano precursors. The kinetics of these reactions were determined and they indicate that the C5 amides were more reactive than their C4 analogs.

  DOI：

  10.1080/07328319908044611
• 作为产物：
  描述：

  5-amino-N'-methoxy-1-methylimidazole-4-carboxamidine 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 氢气 、 双氧水 、 sodium carbonate 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 21.0 ℃ 、101.33 kPa 条件下， 反应 8.5h， 生成 (9ci)-5-氨基-1-甲基-1H-咪唑-4-羧酰胺
  参考文献：
  名称：

  Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides.

  摘要：

  5-氨基-N'-甲氧基-1-甲基咪唑啉-4-甲脒（4a）在1N水合HCl中用NaNO2进行重氮化反应，得到1-甲氧基-2-氮杂腺嘌呤衍生物8a·HI，该物质在处理后与水合Na2CO3反应生成5-叠氮-1-甲基咪唑啉-4-氰化物（5a）。通过类似的重氮化反应从核苷4b得到的核糖类似物5b，被用于合成5-叠氮-1-β-D-呋喃核糖基咪唑啉-4-羧酰胺（9b），这是一种新颖的AICA核苷类似物。在HCONMe2中加热至70°C并保持10分钟，8a·HI生成1-N-氧化物7a。还研究了几种转化5a中功能团的反应。

  DOI：

  10.1248/cpb.42.2263

文献信息

• [EN] BICYCLIC INDOLE-PYRIMIDINE PI3K INHIBITOR COMPOUNDS SELECTIVE FOR P110 DELTA, AND METHODS OF USE<br/>[FR] COMPOSÉS BICYCLIQUES INDOLE-PYRIMIDINE INHIBITEURS DE PI3K SÉLECTIFS POUR P110 DELTA ET LEURS PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010136491A1

  公开（公告）日：2010-12-02

  Formula I (Ia and Ib) compounds wherein (i) X1 is N and X2 is S, (ii) X1 is CR7 and X2 is S, (iii) X1 is N and X2 is NR2, (iv) X1 is CR7 and X2 is O, or (v) X1 is CR7 and X2 is NR2, including stereoisomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PBK, and for treating disorders mediated by lipid kinases such as inflammation, immunological, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  Formula I（Ia和Ib）化合物，其中（i）X1为N且X2为S，（ii）X1为CR7且X2为S，（iii）X1为N且X2为NR2，（iv）X1为CR7且X2为O，或（v）X1为CR7且X2为NR2，包括立体异构体、互变异构体、代谢物及其药学上可接受的盐，用于抑制PBK的δ同工酶，并用于治疗由脂质激酶介导的疾病，如炎症、免疫和癌症。公开了使用Formula I化合物进行体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这些疾病，或相关病理条件的方法。
• [EN] NEW COMPOUNDS AS HSP90 INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS INHIBITEURS DE LA HSP90
  申请人：CRYSTAX PHARMACEUTICALS S L

  公开号：WO2009007399A1

  公开（公告）日：2009-01-15

  The invention provides novel compounds of formula (I) wherein: one of the a, b, c or d members is a nitrogen atom and the remaining members are carbon atoms; and R3 is a radical selected from the group consisting of: -S-R14 and -CH2-R15.The compounds of formula (I) are useful for treating diseases mediated by a heat shock protein 90 (Hsp 90).

  该发明提供了式（I）的新化合物，其中：a、b、c或d成员中的一个是氮原子，其余成员是碳原子；R3是从以下组成的基团中选择的：-S-R14和-CH2-R15。式（I）的化合物对于治疗由热休克蛋白90（Hsp 90）介导的疾病是有用的。
• Synthesis and Characterization of Potential Photolabeling Probes for Studying the Antiviral Mechanisms of EICAR
  作者：Ling Peng、Qiongyou Wu、Jinqiao Wan、Yi Xia、Jiehua Zhou、Fanqi Qu

  DOI：10.3987/com-03-9930

  日期：——

  The designed photolabeling probes: 5-diazonium-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide (1) and 5-azido-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide (2) were synthesized via a short and convenient synthetic route,namely by diazotizing AICAR and subsequently performing substitution with NaN 3 . Although 1 was not stable even at low temperatures, 2 showed a rapid and clean photochemical reaction

  设计的光标记探针：5-重氮-1-β-D-呋喃核糖基-1H-咪唑-4-甲酰胺（1）和5-叠氮基-1-β-D-呋喃核糖基-1H-咪唑-4-甲酰胺（2）通过一种短而方便的合成路线合成，即通过重氮化AICAR并随后用NaN 3 进行取代。尽管 1 即使在低温下也不稳定，但 2 显示出快速而干净的光化学反应，这表明它可能是用于光标记研究的有价值的工具。
• Process for the preparation of 9-substituted guanine derivatives
  申请人：A/S Gea Farmaceutisk Fabrik

  公开号：US05223619A1

  公开（公告）日：1993-06-29

  A process for the preparation of 9-substituted quanine derivatives of general formula (I), in which R is C.sub.1 -C.sub.4 -alkyl optionally substituted with one or more hydroxy groups, or R is (.alpha.), benzyl, ribosyl, 2'-deoxyribosyl or (CH.sub.2).sub.n -OR.sup.1 where n is 1 or 2, and R.sup.1 is CH.sub.2 CH.sub.2 OH or (.beta.) or salts thereof, in which a 1-substituted5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide of general formula (III), where R has the same meaning as in formula (I), is cyclized: a) by treatment with a heavy metal salt of the group of Cu-, Ag-, Pb- and Hg-salts in an aqueous alkaline medium containing at least for equivalents of OH-ions at a temperature form about 0.degree. C. to the reflux temperature, or b) by treatment with a peroxy compound in an aqueous alkaline medium at a temperature of about 0.degree.-30.degree. C., whereafter (I) is isolated by treatment with a acid and, if desired, is converted into a salt. The invention further comprises intermediates for use in the preparation of the above-mentioned compounds.

  一种制备一般式（I）的9-取代基喹啉衍生物的方法，其中R是C.sub.1-C.sub.4-烷基，可选地取代一个或多个羟基，或R是（α）苄基，核糖基，2'-去氧核糖基或（CH.sub.2）.sub.n-OR.sup.1，其中n为1或2，R.sup.1为CH.sub.2 CH.sub.2 OH或（β）或其盐，其中一种一般式（III）的1-取代5-（硫代氨基）-1H-咪唑-4-羧酰胺，其中R的含义与公式（I）中相同，被环化：a）通过在含有至少4当量OH-离子的水性碱性介质中，用Cu-、Ag-、Pb-和Hg-盐的重金属盐处理，在温度为约0℃至沸点温度之间；或b）通过在温度为约0℃至30℃的水性碱性介质中用过氧化物处理，然后通过酸处理分离出（I），如有需要，转化为盐。本发明还包括用于制备上述化合物的中间体。
• PURINYL DERIVATIVES AND THEIR USE AS POTASSIUM CHANNEL MODULATORS
  申请人：Eriksen Birgitte L.

  公开号：US20100105705A1

  公开（公告）日：2010-04-29

  This invention relates to novel purinyl derivatives and their use as potassium channel modulating agents. Moreover the invention is directed to pharmaceutical compositions useful for the treatment or alleviation of diseases or disorders associated with the activity of potassium channels.

  本发明涉及新型嘌呤衍生物及其作为钾通道调节剂的用途。此外，本发明还涉及制备用于治疗或缓解与钾通道活性相关的疾病或疾病的药物组合物。