(9ci)-1-甲基-4-硝基-1H-咪唑-5-羧醛 | 85012-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-1-甲基-4-硝基-1H-咪唑-5-羧醛
• 中文别名: 1-甲基-4-硝基-1H-咪唑-5-甲醛
• 英文名称: 1-methyl-4-nitroimidazole-5-carbaldehyde
• 英文别名: 5-formyl-1-methyl-4-nitro-1H-imidazole；5-formyl-1-methyl-4-nitroimidazole；1-methyl-4-nitro-1H-Imidazole-5-carbaldehyde；3-methyl-5-nitroimidazole-4-carbaldehyde
• CAS: 85012-73-3
• 化学式: C₅H₅N₃O₃
• 分子量: 155.113
• InChiKey: VWTGGHMOJLORHA-UHFFFAOYSA-N

物化性质

• 沸点：
  423.0±30.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9ci)-1-甲基-4-硝基-1H-咪唑-5-羧醛 在 cerium(IV) ammonium nitrate 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 22.33h， 生成 2,6-Dimethyl-4-(1-methyl-4-nitro-imidazol-5-yl)-pyridin-3,5-dicarbonsaeuredimethylester
  参考文献：
  名称：

  Goerlitzer; Klanck, Pharmazie, 1999, vol. 54, # 11, p. 814 - 819

  摘要：

  DOI：
• 作为产物：
  描述：

  5-二氯甲基-1-甲基-4-硝基咪唑 在 silver perchlorate 作用下， 以 水 、 甲苯 为溶剂， 反应 2.5h， 生成 (9ci)-1-甲基-4-硝基-1H-咪唑-5-羧醛
  参考文献：
  名称：

  Ostrowski, S., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2237 - 2248

  摘要：

  DOI：

文献信息

• Synthesis and Antihypertensive Activities of New 1, 4-Dihydropyridine Containing Nitroimidazolyl Substituent with a Nitrooxy Group at the 3-Ester Position
  作者：Abbas Shafiee、Noushin Rastkary、Masoumeh Jorjani、Bijan Shafaghi

  DOI：10.1002/1521-4184(200203)335:2/3<69::aid-ardp69>3.0.co;2-8

  日期：2002.3

  New analogues of nifedipine, in which the ortho nitrophenyl group of position 4 is replaced by 1‐methyl‐4‐nitro‐5‐imidazolyl or 1‐methyl‐5‐imidazolyl with a nitrooxy group at the 3‐ester position were synthesized, and the antihypertensive activity of the compounds was examined by the tail‐cuff method and compared with TNG and nifedipine. Compounds 11g, 11i—11m, 110, 11r, and 11v showed activity similar

  合成了硝苯地平的新类似物，其中 4 位的邻硝基苯基被 1-甲基-4-硝基-5-咪唑基或 1-甲基-5-咪唑基取代，3-酯位具有硝氧基，并且通过尾套法检查化合物的抗高血压活性，并与TNG和硝苯地平进行比较。化合物 11g、11i-11m、110、11r 和 11v 显示出与硝苯地平和 TNG 相似的活性。
• Syntheses of [1,2,3]selenadiazolo[4,5-<i>e</i>]benzofuran or benzothiophene, [1,2,3]thiadiazolo[4,5-<i>e</i>]benzofuran or benzothiophene, and 2-benzofuranyl-1,3,4-oxodiazole derivatives
  作者：M. Shekarchi、F. Ellahiyan、T. Akbarzadeh、A. Shafiee

  DOI：10.1002/jhet.5570400305

  日期：2003.5

  Dehydrogenation of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate 1 with 2,2′-azobi-sisobutyronitrile and N-bromosuccinimide gave ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate 3. Reaction of compounds 3–4 with hydrazine hydrate afforded the corresponding hydrazides 5a-b. The reaction of 5a-b with aldehydes yielded substituted hydrazones 6a-l. Compounds 7a-d were prepared from compounds

  3-甲基-4-氧代-4,5,6,7-四氢苯并呋喃-2-羧酸乙酯1与2,2'-偶氮二-异丁腈和N-溴代琥珀酰亚胺的脱氢得到乙基4-羟基-3-甲基苯并呋喃-2-羧酸3。化合物3-4与水合肼反应，得到相应的酰肼5a-b。5a-b与醛的反应产生取代的6a-1。由化合物6a-d和溴在乙酸中制备化合物7a-d。化合物6e-1的四乙酸铅氧化得到取代的恶二唑8e-1。的4-氧代-4,5,6,7-四氢苯并呋喃缩氨基脲二氧化硒氧化9，图14A和4-氧代-4,5,6,7-四氢苯并噻吩14b中，得到三环1,2,3- selenadiazoles 10，图15A和15b。缩氨基脲的反应图9，图14A和14B与亚硫酰氯，得到相应的1,2,3-噻二唑12，图16A和16B分别。
• Antileishmanial Activities of ( <i>Z</i> )-2-(Nitroimidazolylmethylene)-3( <i>2H</i> )-Benzofuranones: Synthesis, <i>In Vitro</i> Assessment, and Bioactivation by NTR 1 and 2
  作者：Latifeh Navidpour、Marta Lopes Lima、Rachel Milne、Susan Wyllie、Narges Hadj-esfandiari、Muhammad Iqbal Choudhary、Samreen Khan、Sammer Yousuf

  DOI：10.1128/aac.00583-22

  日期：2022.11.15

  Antimicrobial Agents and Chemotherapy, Ahead of Print.

  抗菌剂和化疗，印刷前。
• 艾伏磷酰胺异构体衍生物的合成方法
  申请人：常州大学

  公开号：CN117777196A

  公开（公告）日：2024-03-29

  本发明属于药物合成领域，具体提供了一种艾伏磷酰胺异构体衍生物的合成方法，先以4‑硝基‑1H‑咪唑为原料，经过取代、消除、还原反应生成(1‑烷基‑4‑硝基‑1H‑咪唑‑5‑基)甲醇；然后2‑卤乙胺卤酸盐和三氯氧磷反应，生成N,N'‑双(2‑卤乙基)二氨基膦酸；最后向反应瓶中加入(1‑烷基‑4‑硝基‑1H‑咪唑‑5‑基)甲醇，N,N'‑双(2‑卤乙基)二氨基膦酸，三苯基膦和无水四氢呋喃，体系降至0℃，滴加偶氮二羧酸二异丙酯(DIAD)，升温至25℃反应3h后，减压浓缩得到粗产物，经硅胶柱层析纯化得到艾伏磷酰胺异构体衍生物。
• Synthesis, antibacterial activity, and quantitative structure–activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3()-benzofuranone derivatives
  作者：Narges Hadj-esfandiari、Latifeh Navidpour、Hooman Shadnia、Mohsen Amini、Nasrin Samadi、Mohammad Ali Faramarzi、Abbas Shafiee

  DOI：10.1016/j.bmcl.2007.09.062

  日期：2007.11

  A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities. (C) 2007 Elsevier Ltd. All rights reserved.