4-硝基-1H-咪唑-5-羧酸 | 40507-59-3

• 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 - 有机杂环化合物 - 唑类
• 中文名称: 4-硝基-1H-咪唑-5-羧酸
• 中文别名: 5-硝基咪唑-4-甲酸
• 英文名称: 5-Nitro-1H-imidazole-4-carboxylic Acid
• 英文别名: 5-nitroimidazole-4-carboxylic acid；5-nitro-4-imidazolecarboxylic acid；4-Nitro-1H-imidazole-5-carboxylic acid；5-nitro-1H-imidazole-4-carboxylic acid
• CAS: 40507-59-3
• 化学式: C₄H₃N₃O₄
• mdl: MFCD03013324
• 分子量: 157.086
• InChiKey: IQADWEQLYZUURU-UHFFFAOYSA-N

物化性质

• 熔点：
  304-305 °C
• 沸点：
  580.9±35.0 °C(Predicted)
• 密度：
  1.840±0.06 g/cm3(Predicted)

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：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-硝基-1H-咪唑-5-羧酸 在 氯化亚砜 作用下， 反应 2.0h， 生成 1,6-dinitro-5H,10H-diimidazo<1,5-a:1',5'-d>pyrazine-5,10-dione
  参考文献：
  名称：

  IMIDAZOTETRAZINONE-BASED COMBI-MOLECULES

  摘要：

  这里描述了一系列展示抗肿瘤活性的新化学试剂。这些新化学试剂表现出双重抗肿瘤作用方式：阻断表皮生长因子受体（EGFR）介导的信号传导，并通过烷基化损害DNA。

  公开号：

  US20120283280A1
• 作为产物：
  描述：

  1H-咪唑-4-甲酸 在 硝酸铵 、 硫酸 作用下， 反应 12.0h， 以73%的产率得到4-硝基-1H-咪唑-5-羧酸
  参考文献：
  名称：

  IMIDAZOTETRAZINONE-BASED COMBI-MOLECULES

  摘要：

  这里描述了一系列展示抗肿瘤活性的新化学试剂。这些新化学试剂表现出双重抗肿瘤作用方式：阻断表皮生长因子受体（EGFR）介导的信号传导，并通过烷基化损害DNA。

  公开号：

  US20120283280A1

文献信息

• Analogs of iso-azepinomycin as potential transition-state analog inhibitors of guanase: Synthesis, biochemical screening, and structure–activity correlations of various selectively substituted imidazo[4,5-e][1,4]diazepines
  作者：Saritha Tantravedi、Saibal Chakraborty、Niti H. Shah、James C. Fishbein、Ramachandra S. Hosmane

  DOI：10.1016/j.bmc.2013.06.069

  日期：2013.9

  transition state analog inhibitor of guanase, does not represent the true transition state of the enzyme-catalyzed reaction as closely as does iso-azepinomycin, wherein the 6-hydroxy group of azepinomycin has been translocated to the 5-position. Based on this hypothesis, and assuming that iso-azepinomycin would bind to guanase at the same active site as azepinomycin, several analogs of iso-azepinomycin

  胍酶是核酸代谢嘌呤补救途径的重要酶，其抑制作用对病毒、细菌和癌症治疗具有有益意义。本文描述的工作基于这样一个假设，即阿西平霉素，一种杂环天然产物和所谓的胍酶过渡态类似物抑制剂，并不像异阿西平霉素那样代表酶催化反应的真实过渡态，其中 6 azepinomycin 的 - 羟基已转移到 5 位。基于这一假设，并假设ISO -azepinomycin将绑定在相同的活性位点的azepinomycin以鸟嘌呤酶，几个类似物异-azepinomycin 被设计并成功合成，以初步了解配体的胍酶结合位点周围的疏水和亲水位点。具体而言，类似物被设计为探索异氮杂霉素的N1、N3和N4氮原子以及O 5氧原子附近的疏水袋(如果有的话)。使用哺乳动物胍酶进行这些类似物的生化抑制研究。我们的结果表明 (1) 增加 O 5附近的疏水性导致负面影响，(2) 将疏水性从 N3 转移到 N1 也会导致抑制降低，(3) 增加 N3
• Synthesis of novel derivatives of 2-(azolylimino)thiazoline
  作者：O. S. Eltsov、V. S. Mokrushin、A. V. Tkachev

  DOI：10.1007/s11172-005-0116-8

  日期：2004.10

  Successive alkylation of 5-(3-phenylthioureido)-3H-imidazole-4-carboxamides with alkyl halides and chloroacetone gave (N-oxopropylimidazolyl)isothioureas, which were easily converted into derivatives of purine and imidazopyrazinone. In the case of ethyl 5-(3-phenylthioureido)-3H-imidazole-4-carboxylate, primary alkylation occurs at the N atom of the imidazole ring. Reactions of 5-(3-phenylthiourei

  5-(3-苯基硫脲基)-3H-咪唑-4-甲酰胺与卤代烷和氯丙酮的连续烷基化得到(N-氧代丙基咪唑基)异硫脲，其很容易转化为嘌呤和咪唑并吡嗪酮的衍生物。在 5-(3-苯基硫脲基)-3H-咪唑-4-羧酸乙酯的情况下，初级烷基化发生在咪唑环的 N 原子上。5-(3-苯基硫脲基)-3H-咪唑-4-甲酰胺与卤代酮反应得到许多4-羟基-2-咪唑基亚胺噻唑烷和2-咪唑基亚氨基-Δ4-噻唑啉。
• Tetrazine derivatives
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05260291A1

  公开（公告）日：1993-11-09

  [ 3H]-Imidazo[ 5,1-d] -1,2,3,5-tetrazin-4-one derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen, or an alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms, each such group being unsubstituted or substituted by from one to three substituents selected from halogen atoms, alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl groups containing up to 4 carbon atoms, and optionally substituted phenyl groups, or R.sup.1 represents a cycloalkyl group containing from 3 to 8 carbon atoms, and R.sup.2 represents a carbamoyl group optionally N-substituted by one or two groups selected ftom alkyl and alkenyl groups containing up to 4 carbon atoms, and cycloalkyl groups containing 3 to 8 carbon atoms, are new therapeutically useful compounds possessing antineoplastic and immunomodulatory activity.

  该公式的[3H]-Imidazo[5,1-d]-1,2,3,5-四唑-4-酮衍生物：其中R1代表氢，或者是含有最多6个碳原子的烷基，烯基或炔基，每个这样的基团未被取代或被从卤素原子，烷氧基，烷硫基，烷基亚磺酰基和烷基磺酰基中选择的1到3个取代基取代，这些取代基含有最多4个碳原子，并且可以是取代的苯基，或R1代表含有3到8个碳原子的环烷基，R2代表一个氨基甲酰基团，该氨基甲酰基团可以被一个或两个选择自含有最多4个碳原子的烷基和烯基团和含有3到8个碳原子的环烷基的基团取代，是新的具有抗肿瘤和免疫调节活性的治疗上有用的化合物。
• Allsebrook et al., Journal of the Chemical Society, 1942, p. 232,233
  作者：Allsebrook et al.

  DOI：——

  日期：——
• Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones
  作者：Edward Lunt、Christopher G. Newton、Christopher Smith、Graham P. Stevens、Malcolm F. G. Stevens、Colin G. Straw、Roger J. A. Walsh、Peter J. Warren、Christian Fizames

  DOI：10.1021/jm00385a018

  日期：1987.2

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.