4-氯甲基咪唑 | 23785-22-0

• 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-氯甲基咪唑
• 英文名称: 4-chloromethylimidazole
• 英文别名: 4-Chlormethyl-imidazol；4-imidazolylmethyl chloride；5-(chloromethyl)-1H-imidazole
• CAS: 23785-22-0
• 化学式: C₄H₅ClN₂
• 分子量: 116.55
• InChiKey: HCGYTFXTHWTYFK-UHFFFAOYSA-N

物化性质

• 沸点：
  328.8±17.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯甲基咪唑 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以40%的产率得到4-(azidomethyl)-1H-imidazole
  参考文献：
  名称：

  Fluconazole analogues with metal-binding motifs impact metal-dependent processes and demonstrate antifungal activity in Candida albicans

  摘要：

  Azole antifungals are an important class of antifungal drugs due to their low cost, ability to be administered orally, and broad-spectrum activity. However, their widespread and long-term use have given rise to adaptation mechanisms that render these compounds less effective against common fungal pathogens, includingCandida albicans. New antifungals are desperately needed as drug-resistant strains become more prevalent. We recently showed that copper supplementation potentiates the activity of the azole antifungal fluconazole against the opportunistic fungal pathogenC. albicans. Here, we report eight new azole analogues derived from fluconazole in which one triazole group has been replaced with a metal-binding group, a strategy designed to enhance potentiation of azole antifungal activity by copper. The bioactivity of all eight compounds was tested and compared to that of fluconazole. Three of the analogues showed activity againstC. albicansand two had lower levels of trailing growth. One compound, Flu-TSCZ, was found to impact the levels, speciation, and bioavailability of cellular metals.[GRAPHICS].

  DOI：

  10.1007/s00775-020-01796-x
• 作为产物：
  描述：

  4-羟甲基咪唑盐酸盐 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 4-氯甲基咪唑
  参考文献：
  名称：

  Syntheses of imidazole-acridine conjugates as ribonuclease A mimics

  摘要：

  As a result of efforts to mimic the activity of RNase A we report the syntheses of two novel molecules 1 and 2 containing imidazole residues conjugated to an acridine, a well known intercalator and as such these molecules simultaneously have substrate recognition and potential catalytic ability. t-RNA cleavage by I and 2 is reported. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00843-x

文献信息

• [EN] SUBSTITUTED IMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS<br/>[FR] IMIDAZOLE CARBOXAMIDES SUBSTITUÉS ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES MÉDICAUX
  申请人：BIAL BIOTECH INVEST INC

  公开号：WO2021055612A1

  公开（公告）日：2021-03-25

  The invention provides substituted imidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

  这项发明提供了替代咪唑羧酰胺及相关化合物，含有这些化合物的组合物，医疗工具包，以及使用这些化合物和组合物治疗患者的医疗障碍，例如癌症、溶酶体贮积症、神经退行性疾病、炎症性疾病等的方法。
• 4-Benzyl- and 4-benzoyl-substituted imidazole derivatives and use as
  申请人：Farmos-Yhtyma OY (Farmos Group Ltd.)

  公开号：US04443466A1

  公开（公告）日：1984-04-17

  The invention provides compounds of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which can be the same or different, are each hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy or nitro; R.sub.4 is hydrogen or alkyl of 1 to 7 carbon atoms; --X-- is ##STR2## R.sub.5 is hydrogen, hydroxy or --OR.sub.6 ; and R.sub.6 is alkyl of 1 to 7 carbon atoms or aryl of 6 to 10 carbon atoms; and their non-toxic pharmaceutically acceptable acid addition salts and mixtures thereof. Processes for the preparation and use of the subject compounds are described, as are novel pharmaceutical compositions comprising at least one of the subject compounds or their salts. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are useful in the treatment of mammals, e.g., as anti-ulcer or anti-hypertensive agents. Furthermore, they are useful as diuretic, sedative, analgesic, anti-inflammatory and tranquilizing agents.

  该发明提供了以下结构的化合物：其中R.sub.1、R.sub.2和R.sub.3可以相同也可以不同，分别是氢、氯、溴、氟、甲基、乙基、甲氧基、氨基、羟基或硝基；R.sub.4是氢或1至7个碳原子的烷基；--X--是；R.sub.5是氢、羟基或--OR.sub.6；R.sub.6是1至7个碳原子的烷基或6至10个碳原子的芳基；以及它们的无毒药学上可接受的酸加盐和混合物。描述了制备和使用这些化合物的方法，以及包含至少一种这些化合物或其盐的新型药物组合物。这些化合物及其无毒盐表现出有价值的药理活性，并在治疗哺乳动物方面具有用途，例如作为抗溃疡或抗高血压剂。此外，它们还可作为利尿剂、镇静剂、镇痛剂、抗炎剂和镇定剂。
• Imidazole compounds and their therapeutic applications
  申请人：Institut National de la Sante et de la Recherche Medicale

  公开号：US05559113A1

  公开（公告）日：1996-09-24

  A compound selected from the group consisting of a compound of the formula ##STR1## wherein the substituents are defined as in the specification having antagonist properties to histamine H.sub.3 -receptors.

  从以下化合物组合中选择的一种化合物，其化学式为##STR1##其中取代基的定义如规范中所述，具有对组织胺H.sub.3受体的拮抗性能。
• Imidazole derivatives for pharmaceutical use
  申请人：Institut National de la Sante et de la Recherche Medicale

  公开号：US05708171A1

  公开（公告）日：1998-01-13

  A compound selected from the group consisting of a compound of the formula ##STR1## having antagonist properties to histamine H.sub.3 -receptors.

  从以下化合物组中选择的一种化合物，具有对组胺H.sub.3受体的拮抗作用的化合物，其化学式为##STR1##。
• Dual inhibitors of farnesyltransferase and geranylgeranyltransferase I
  申请人：H. Lee Moffitt Cancer Center and Research Institute, Inc.

  公开号：US09040563B2

  公开（公告）日：2015-05-26

  Many GTPases such as Ras, Ral and Rho require post-translational farnestylation or geranylgeranylation for mediating malignant transformation. Dual farnesyltransferase (FT) (FTI) and geranylgeranyltransferase-I (GGT-1) inhibitors (GGTI) were developed as anticancer agents from based on an ethylenediamine scaffold. On the basis of a 4-fold substituted ethylenediamine scaffold, the inhibitors are structurally simple and readily derivatized, facilitating extensive structure-activity relationship studies. The most potent inhibitor is compound exhibited an in vitro hFTase IC50 value of 25 nM and a whole cell H-Ras processing IC50 value of 90 nM. Several of the inhibitors proved highly selective for hFTase over the related prenyltransferase enzyme geranylgeranyltransferase-I (GGTase-I). A crystal structure of an inhibitor cocrystallized with farnesyl pyrophosphate in the active site of rat FTase illustrates that the para-benzonitrile moiety is stabilized by a π-π stacking interaction with the Y361β residue, suggesting an importance of this component of the inhibitors.

  许多GTP酶，如Ras、Ral和Rho，需要经过翻译后的法尼酰化或戊二烯基化才能介导恶性转化。基于乙二胺支架，开发了双法尼基转移酶（FT）（FTI）和戊二烯基转移酶-I（GGT-1）抑制剂（GGTI）作为抗癌药物。这些抑制剂的结构简单，易于衍生，便于进行广泛的结构活性关系研究。其中最有效的抑制剂在体外hFTase IC50值为25 nM，全细胞H-Ras处理IC50值为90 nM。其中几种抑制剂对相关的戊二烯基转移酶酶高度选择性。一种抑制剂与法尼酰焦磷酸在大鼠FTase的活性位点上共结晶的晶体结构表明，对苯二腈基团与Y361β残基的π-π堆叠相互作用稳定，这表明该抑制剂的这个组分很重要。