methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate | 115444-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate
• 英文别名: Ethyl 2-methyl-1H-benzimidazole-1-butanoate；ethyl 4-(2-methylbenzimidazol-1-yl)butanoate
• CAS: 115444-75-2
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: ZKYVLQJAWRQGGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  153-158 °C
• 沸点：
  406.9±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以82.5%的产率得到4-(2-甲基-1H-苯并咪唑-1-基)丁酸
  参考文献：
  名称：

  Synthesis and application of imidazole derivatives. Synthesis of 5-methyl-7,8,9,10-tetrahydro-5H-azepino(1,2-a)benzimidazol-4-one and related compounds.

  摘要：

  在三乙胺存在下，将 1-(3-羧丙基)-2，3-二甲基苯并咪唑鎓碘化物 (11) 与 1，1'-羰基二咪唑处理，合成了 5-甲基-7，8，9，10-四氢-5H-氮杂卓[1，2-α]苯并咪唑-7-酮 (6)。在乙酸乙酯中回流 2-（5-氯-2-氧代戊基）-1-甲基苯并咪唑（4）不能得到 6，但得到了(Z)-1-甲基-2-（2, 3, 4, 5-四氢-2-亚呋喃甲基）苯并咪唑（5），在碱式氧化铝存在下，在乙酸乙酯中加热，重新排列成相应的(E)-异构体（7）。5、6 和 7 的结构是通过 X 射线晶体学确定的。

  DOI：

  10.1248/cpb.38.301
• 作为产物：
  描述：

  2-甲基苯并咪唑 、 4-溴丁酸乙酯 在 sodium hydride 作用下， 生成 methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate
  参考文献：
  名称：

  Synthesis and application of imidazole derivatives. Synthesis of 5-methyl-7,8,9,10-tetrahydro-5H-azepino(1,2-a)benzimidazol-4-one and related compounds.

  摘要：

  在三乙胺存在下，将 1-(3-羧丙基)-2，3-二甲基苯并咪唑鎓碘化物 (11) 与 1，1'-羰基二咪唑处理，合成了 5-甲基-7，8，9，10-四氢-5H-氮杂卓[1，2-α]苯并咪唑-7-酮 (6)。在乙酸乙酯中回流 2-（5-氯-2-氧代戊基）-1-甲基苯并咪唑（4）不能得到 6，但得到了(Z)-1-甲基-2-（2, 3, 4, 5-四氢-2-亚呋喃甲基）苯并咪唑（5），在碱式氧化铝存在下，在乙酸乙酯中加热，重新排列成相应的(E)-异构体（7）。5、6 和 7 的结构是通过 X 射线晶体学确定的。

  DOI：

  10.1248/cpb.38.301

文献信息

• [EN] COMPOSITIONS FOR TRANSFECTING A NUCLEIC ACID MOLECULE INTO A CELL COMPRISING HETEROCYCLIC COMPOUNDS GRAFTED TO A CATIONIC POLYMER, AND THEIR APPLICATIONS<br/>[FR] COMPOSITIONS POUR LA TRANSFECTION D'UNE MOLÉCULE D'ACIDE NUCLÉIQUE DANS UNE CELLULE COMPRENANT DES COMPOSÉS HÉTÉROCYCLIQUES GREFFÉS À UN POLYMÈRE CATIONIQUE ET LEURS APPLICATIONS
  申请人：POLYPLUS TRANSFECTION

  公开号：WO2021023796A1

  公开（公告）日：2021-02-11

  The present invention relates to compositions for transfecting a nucleic acid molecule into a cell and their applications. The present invention is directed to a composition suitable for transfecting a nucleic acid molecule into a cell, preferably a eukaryotic cell, comprising (i) at least one compound of general formula (II) or a tautomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or an acceptable salt thereof, and (ii) an acceptable excipient, buffering agent, cell culture medium, or transfection medium, wherein Y1, Y2, Y3, Z1, Z2, Z3, Z4, Z5, Z6, Z7, X1, X2, R3, P+, R, T, U and V are as defined in the description. The present invention also relates to uses of said composition and to a method for in vitro or ex vivo transfection of live cells.

  本发明涉及用于将核酸分子转染入细胞的组合物及其应用。本发明涉及一种适用于将核酸分子转染入细胞，特别是真核细胞的组合物，包括（i）至少一种一般式（II）的化合物或其互变异构体、互变异构体、外消旋体、对映体、非对映体或其混合物，或其可接受的盐，以及（ii）可接受的赋形剂、缓冲剂、细胞培养基或转染培养基，其中Y1、Y2、Y3、Z1、Z2、Z3、Z4、Z5、Z6、Z7、X1、X2、R3、P+、R、T、U和V的定义如描述中所述。本发明还涉及所述组合物的用途以及一种用于体外或体内细胞转染的方法。
• Structure–Activity Studies of Divin: An Inhibitor of Bacterial Cell Division
  作者：Maoquan Zhou、Ye-Jin Eun、Ilia A. Guzei、Douglas B. Weibel

  DOI：10.1021/ml400234x

  日期：2013.9.12

  We describe the synthesis and structure activity relationship (SAR) studies of divin, a small molecule that blocks bacterial division by perturbing the assembly of proteins at the site of cell septation. The bacteriostatic mechanism of action of divin is distinct from other reported inhibitors of bacterial cell division and provides an opportunity for assessing the therapeutic value of a new class of antimicrobial agents. We demonstrate a convenient synthetic route to divin and its analogues, and describe compounds with a 10-fold increase in solubility and a 4-fold improvement in potency. Divin analogues produce a phenotype that is identical to divin, suggesting that their biological activity comes from a similar mechanism of action. Our studies indicate that the 2-hydroxynaphthalenyl hydrazide portion of divin is essential for its activity and that alterations and substitution to the benzimidazole ring can increase its potency. The SAR study provides a critical opportunity to isolate drug resistant mutants and synthesize photoaffinity probes to determine the cellular target and biomolecular mechanism of divin.
• Azino-Fused Benzimidazolium Salts as DNA Intercalating Agents. 2.
  作者：Joaquín Pastor、Jorge G. Siro、José L. García-Navío、Juan J. Vaquero、Julio Alvarez-Builla、Federico Gago、Beatriz de Pascual-Teresa、Manuel Pastor、M. Melia Rodrigo

  DOI：10.1021/jo962055i

  日期：1997.8.1

  The synthesis of new pyrido[1,2-a]- and pyridazino[1,6-a]benzimidazolium salts by basic condensation of 1,3-disubstituted 2-alkylbenzimidazolium salts and 1,2-diketones and subsequent chemical transformations is described. The DNA-binding properties were examined by UV-vis spectroscopy, viscosimetric determinations, and molecular modeling techniques. The presence of a flat polycyclic hydrocarbon moiety such as a naphthalene-1,8-diyl or a biphenyl-o,o'-diyl, fused to the cationic heterocycle, appears to enhance the interaction with DNA. Variation of the substituents on the indole-like N will allow us to build up a new series of his-salts with bis-intercalating properties.
• OHTA, SHUNSAKU;NARITA, YOSHIHIRO;OKAMOTO, MASAO;HATAKEYAMA, SHOKO;KAN, KE+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 301-306
  作者：OHTA, SHUNSAKU、NARITA, YOSHIHIRO、OKAMOTO, MASAO、HATAKEYAMA, SHOKO、KAN, KE+

  DOI：——

  日期：——
• OKAMOTO, MACAO
  作者：OKAMOTO, MACAO

  DOI：——

  日期：——