1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride | 49575-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride
• 英文别名: 2-(2-Methyl-5-nitro-1h-imidazol-1-yl)ethanamine hydrochloride；2-(2-methyl-5-nitroimidazol-1-yl)ethanamine;hydrochloride
• CAS: 49575-10-2
• 化学式: C₆H₁₀N₄O₂*2ClH
• 分子量: 243.093
• InChiKey: VKGNYWVXNRYHTN-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 溶解度：
  可溶于二甲基亚砜、甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37,S45
• 危险类别码：
  R22,R40
• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride 在 氯磺酰异氰酸酯 、 三乙胺 、 叔丁醇 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以70%的产率得到N-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]sulfamide
  参考文献：
  名称：

  [EN] CANCER TARGETING USING CARBONIC ANHYDRASE ISOFORM IX INHIBITORS
  [FR] CIBLAGE DE CANCER UTILISANT DES INHIBITEURS D'ISOFORME IX D'ANHYDRASE CARBONIQUE

  摘要：

  公开号：

  WO2012087115A8
• 作为产物：
  描述：

  2-甲基-5-硝基-1H-咪唑-1-乙基甲磺酸酯 在 盐酸 、 sodium azide 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride
  参考文献：
  名称：

  Hay; Wilson; Moselen, Journal of Medicinal Chemistry, 1994, vol. 37, # 3, p. 381 - 391

  摘要：

  DOI：

文献信息

• [EN] MTH1 INHIBITORS FOR TREATMENT OF CANCER<br/>[FR] INHIBITEURS MTH1 POUR LE TRAITEMENT DU CANCER
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2015187088A1

  公开（公告）日：2015-12-10

  A compound of formula I, (I) or a pharmaceutically-acceptable salt thereof. The compound is useful in the treatment of cancer.

  公式I的化合物(I)或其药用可接受的盐。该化合物在治疗癌症中很有用。
• Crystal Habit Modification of Metronidazole by Supramolecular Gels with Complementary Functionality
  作者：Sreejith Sudhakaran Jayabhavan、Jonathan W. Steed、Krishna K. Damodaran

  DOI：10.1021/acs.cgd.1c00659

  日期：2021.9.1

  A series of bis(urea) compounds with complementary functional groups similar to the pharmaceutical drug metronidazole and a structural isomer isometronidazole have been synthesized. The gelation properties of these compounds were studied in various solvent/solvent mixtures. The mechanical strength of the isomeric gelators was compared using rheology, and the morphologies of the xerogels were analyzed by scanning electron microscopy. These gels were used as media for metronidazole crystallization resulting in a marked habit modification of the metronidazole crystals in the drug-mimicking gels. However, crystallization in the nonmimetic isomeric gel resulted in morphologies similar to the solution state. These results indicate that the drug-mimetic gels interact with the surface of the drug crystal giving rise to new morphologies.

  合成了一系列具有与药物甲硝唑相似的互补功能团的双（脲）化合物及其结构异构体异甲硝唑。研究了这些化合物在不同溶剂/溶剂混合物中的成胶特性。使用流变学比较了异构体凝胶剂的机械强度，并通过扫描电子显微镜分析了干凝胶的形态。这些凝胶被用作甲硝唑结晶的介质，导致在类药物凝胶中甲硝唑晶体的形态发生显著变化。然而，在非类药物异构体凝胶中的结晶结果显示出与溶液状态类似的形态。这些结果表明，类药物凝胶与药物晶体的表面相互作用，从而产生了新的形态。
• DIAGNOSTIC AGENT FOR INFECTIOUS DISEASES
  申请人：Sakurai Kazuhisa

  公开号：US20120219500A1

  公开（公告）日：2012-08-30

  A diagnostic agent for infectious diseases which is capable of distinguishing among different kinds of bacterial species and which allows simple and non-invasive measurement and/or imaging in a short period of time is provided; and a screening method for a therapeutic agent for infectious diseases caused by microorganisms are provided. A diagnostic agent for infectious diseases caused by nitroimidazole susceptible microorganisms, containing an imidazole derivative or a fused imidazole derivative having at least one nitro group on an imidazole ring, or a labeled form thereof as an active ingredient is provided.

  提供了一种针对传染病的诊断试剂，能够区分不同种类的细菌，并允许在短时间内进行简单、非侵入性的测量和/或成像；同时提供了一种筛选治疗由微生物引起的传染病的方法。提供了一种针对对硝基咪唑敏感微生物引起的传染病的诊断试剂，其包含一种咪唑衍生物或至少在咪唑环上具有一个硝基基团的融合咪唑衍生物，或其标记形式作为活性成分。
• Porphyrin-linked nitroimidazole antibiotics targeting Porphyromonas gingivalis
  作者：Benjamin C.-M. Yap、Grace L. Simpkins、Charles A. Collyer、Neil Hunter、Maxwell J. Crossley

  DOI：10.1039/b904340c

  日期：——

  Periodontal disease is an inflammatory process affecting supporting tissues surrounding the teeth. The anaerobic Gram-negative bacterium Porphyromonas gingivalis is implicated in the disease. This organism requires the uptake of porphyrins most apparently as haem 1 from local haemorrhage and it has a HA2 receptor on the outer membrane for this purpose that provides the opportunity to achieve selective anti-microbial activity. Uniquely, this receptor is based on recognition of porphyrin macrocycle and on a propionic acid side-chain rather than recognition of the coordinated metal ion through chelation, a process used by other organisms with the HasA porphyrin receptor. Porphyrin–antibiotic conjugates 11, 12, 13a and 13b were designed as potential highly selective P. gingivalisinhibitors, a key point being that they are based on the use of free-base porphyrins to render them unpalatable to other organisms. These compounds were synthesised from metronidazole 4 and deuteroporphyrin IX 3. Conjugates 11, 12, 13a and 13b are all recognised by the HA2 receptor of P. gingivalis, bind as strongly as haem 1 to HA2 and are highly effective. For example, the amide-linked mono-metronidazole mono-acid adducts 11 and 12 have the same growth inhibitory activity towards P. gingivalis and both are two-fold more active than metronidazole 4 and ten- to twenty-fold more effective than the metronidazole derivative, amine 5. The methyl esters 9 and 10, in contrast, are not recognised by HA2 and are ineffective in inhibiting P. gingivalis, leading to the conclusion that capture by HA2 may be necessary for activity of the adducts. Preliminary growth inhibition assays involving a range of bacteria have demonstrated the high selectivity of conjugates 13a and 13b towards P. gingivalis.

  牙周病是一种影响牙齿周围支持组织的炎症过程。厌氧革兰阴性菌牙龈卟啉单胞菌与牙周病有关。这种细菌需要吸收卟啉，最明显的是吸收局部出血中的血红素 1，为此，它的外膜上有一个 HA2 受体，为实现选择性抗微生物活性提供了机会。与众不同的是，这种受体是基于对卟啉大环和丙酸侧链的识别，而不是通过螯合作用识别配位金属离子，其他生物使用的是 HasA 卟啉受体。卟啉-抗生素共轭物 11、12、13a 和 13b 被设计为潜在的高选择性牙龈卟啉抑制剂，关键在于它们基于游离基卟啉的使用，使其对其他生物无味。这些化合物是由甲硝唑 4 和氘代卟啉 IX 3 合成的。共轭物 11、12、13a 和 13b 都能被牙龈脓胞的 HA2 受体识别，与血红素 1 与 HA2 的结合力一样强，而且非常有效。例如，酰胺连接的单甲硝唑单酸加合物 11 和 12 对牙龈脓胞具有相同的生长抑制活性，其活性都比甲硝唑 4 高出 2 倍，比甲硝唑衍生物胺 5 高出 10 到 20 倍。与此相反，甲酯 9 和 10 不能被 HA2 识别，对牙龈脓毒性无效，由此得出的结论是，HA2 的捕获可能是加合物活性的必要条件。涉及一系列细菌的初步生长抑制试验表明，共轭物 13a 和 13b 对牙龈脓疱病菌具有很高的选择性。
• Synthesis and biological evaluation of a novel asymmetrical99mTc-nitrido complex of metronidazole derivative
  作者：Dejing Kong、Jie Lu、Shuzhang Ye、Xuebin Wang

  DOI：10.1002/jlcr.1292

  日期：2007.11

  radiochemical purity of the product was above 95% as measured by thin-layer chromatography and high-performance liquid chromatography. In vitro studies showed that the complex possessed good stability under physiological conditions. Its partition coefficient studies indicated that it was a lipophilic complex. The electrophoresis results showed that the complex was cationic. Biological evaluation of the complex

  甲硝唑的新型二硫代氨基甲酸酯衍生物 2-(2-甲基-5-硝基-1H-咪唑基)-乙基-二硫代氨基甲酸钾 (MNIE-DTC) 被合成为含有药效团的双功能配体。通过添加双膦配体 PNP5 (PNP5 = N-乙氧乙基-N,N-双[2-(双(3-甲氧基丙基)膦基) ) 乙基]-胺) 和二硫代氨基甲酸酯配体 (MNIE-DTC) 在 100°C 下加入 99mTc-硝基前体溶液 15 分钟。产品经薄层色谱和高效液相色谱测定，放射化学纯度在95%以上。体外研究表明，该配合物在生理条件下具有良好的稳定性。其分配系数研究表明它是一种亲脂性复合物。电泳结果表明配合物为阳离子型。对复合物[99mTcN(PNP5)(MNIE-DTC)]+在携带H22肿瘤的昆明小鼠中进行的生物学评估表明，该复合物具有中等的肿瘤摄取（0.57±0.06%ID/g at 1h），并且/血液和肿瘤/肌肉在注射后1小时分别为2.46和1