(1-甲基-1H-苯并咪唑-2-基)乙酸乙酯 | 2735-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (1-甲基-1H-苯并咪唑-2-基)乙酸乙酯
• 英文名称: ethyl 2-(1-methylbenzimidazol-2-yl)acetate
• 英文别名: ethyl (1-methyl-2-benzimidazolyl)acetate；ethyl 1-methylbenzimidazole-2-acetate；(1-methyl-1H-benzoimidazol-2-yl)-acetic acid ethyl ester；ethyl 2-(1-methylbenzimidazol-2-yl) acetate；ethyl 2-(1-methylbenzimidazol-2-yl)-acetate；<1-Methyl-benzimidazolyl-(2)>-essigsaeure-ethylester；(1-Methyl-1H-benzoimidazol-2-yl)acetic acid ethyl ester
• CAS: 2735-61-7
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: LFYJEKQLJRNBQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (1-甲基-1H-苯并咪唑-2-基)乙酸乙酯 在 三氯硫氯甲烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以31%的产率得到ethyl 2,2-dichloro-2-(1-methylbenzimidazol-2-yl)acetate
  参考文献：
  名称：

  McKinnon, David M.; Spevack, Perry; Tipples, Graham, Canadian Journal of Chemistry, 1988, vol. 66, p. 2339 - 2344

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基-1,2-苯二胺 、 丙二酸二乙酯 以63%的产率得到
  参考文献：
  名称：

  MCKINNON, DAVID M.;SPEVACK, PERRY;TIPPLES, GRAHAM, CAN. J. CHEM., 66,(1988) N, C. 2339-2344

  摘要：

  DOI：

文献信息

• Amide derivatives and medicinal compositions thereof
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06048884A1

  公开（公告）日：2000-04-11

  An amide derivative represented by the following general formula (I) or a salt thereof and a pharmaceutical composition containing the amide derivative and a pharmaceutically acceptable vehicle. ##STR1## (The symbols in the formula have the following meanings. (wherein A: heteroarylene; X: bond, O, S, --NR.sup.5 --, --NR.sup.5 CO--, --NR.sup.5 CONH--, --NR.sup.5 SO.sub.2 -- or --NR.sup.5 C(.dbd.NH)NH--; R.sup.1 : --H, -optionally substituted lower alkyl, -optionally substituted aryl, -optionally substituted heteroaryl or -optionally substituted cycloalkyl; R.sup.2a, R.sup.2b : --H or -lower alkyl, which may be the same or different; R.sup.3 : --H or -lower alkyl; R.sup.4a, R.sup.4b : --H or --OH, which may be the same different, or R.sup.4a and R.sup.4b are taken together to form .dbd.O or .dbd.N.about.O-lower alkyl; and R.sup.5 : --H or -lower alkyl.)

  以下是由下列一般式（I）表示的酰胺衍生物或其盐以及含有该酰胺衍生物和药用可接受载体的药物组合物。##STR1##（式中符号的含义如下。（其中A：杂芳烃；X：键，O，S，-NR.sup.5-，-NR.sup.5 CO-，-NR.sup.5 CONH-，-NR.sup.5 SO.sub.2-或-NR.sup.5 C(.dbd.NH)NH-；R.sup.1：-H，-可选择地取代的较低烷基，-可选择地取代的芳基，-可选择地取代的杂芳基或-可选择地取代的环烷基；R.sup.2a，R.sup.2b：-H或-较低烷基，可以相同也可以不同；R.sup.3：-H或-较低烷基；R.sup.4a，R.sup.4b：-H或-OH，可以相同也可以不同，或R.sup.4a和R.sup.4b一起形成.dbd.O或.dbd.N.about.O-较低烷基；以及R.sup.5：-H或-较低烷基。）
• Synthesis of Fused Imidazole-Containing Ring Systems via Dual Oxidative Amination of C(sp³)–H Bonds
  作者：Georgette Castanedo、Yanzhou Liu、James J. Crawford、Marie-Gabrielle Braun

  DOI：10.1021/acs.joc.6b01517

  日期：2016.9.16

  A general and efficient method for a metal-free one-pot synthesis of highly substituted fused imidazole-containing 5,5- and 5,6-fused bicyclic heterocycles is described. Starting from commercially available substrates and reagents, the reaction proceeds through two C–N bond formations and an oxidative dehydrogenation to form highly substituted products in good to excellent yield.

  描述了一种通用且有效的方法，用于无金属一锅合成高度取代的稠合的含咪唑的5,5-和5,6-稠合的双环杂环。从可商购的底物和试剂开始，该反应通过两个C–N键的形成和氧化脱氢进行，以形成高取代率的产品，收率好至极好。
• NOVEL AMIDE DERIVATIVES AND MEDICINAL COMPOSITIONS THEREOF
  申请人：YAMANOUCHI PHARMACEUTICAL CO., LTD.

  公开号：EP0972769A1

  公开（公告）日：2000-01-19

  An amide derivative represented by the following general formula (I) or a salt thereof and a pharmaceutical composition containing the amide derivative and a pharmaceutically acceptable vehicle. (The symbols in the formula have the following meanings. (wherein A:heteroarylene; X:bond, O, S, -NR5-, -NR5CO-, -NR5CONH-, -NR5SO2- or -NR5C(=NH)NH-; R1:-H, -optionally substituted lower alkyl, -optionally substituted aryl, -optionally substituted heteroaryl or -optionally substituted cycloalkyl; R2a, R2b:-H or -lower alkyl, which may be the same or different; R3:-H or -lower alkyl; R4a, R4b:-H or -OH, which may be the same different, or R4a and R4b are taken together to form =O or =N∼O-lower alkyl; and R5:-H or -lower alkyl.)

  由以下通式（I）代表的酰胺衍生物或其盐，以及含有该酰胺衍生物和药学上可接受的载体的药物组合物。 (式中符号含义如下。其中 A:杂芳基； X:键、O、S、-NR5-、-NR5CO-、-NR5CONH-、-NR5SO2-或-NR5C(=NH)NH-； R1：-H、-任选取代的低级烷基、-任选取代的芳基、-任选取代的杂芳基或-任选取代的环烷基； R2a、R2b：-H 或-低级烷基，它们可以相同或不同； R3：-H 或-低级烷基； R4a、R4b：-H 或 -OH，它们可以相同或不同，或者 R4a 和 R4b 合在一起形成 =O 或 =N∼O 低级烷基；以及 R5：-H 或-低级烷基）。
• Compositions, uses and methods for making them
  申请人：PIMERA, INC.

  公开号：US10590134B2

  公开（公告）日：2020-03-17

  Generally, the present invention provides novel quinolone compounds and pharmaceutical composition thereof which may inhibit cell proliferation and/or induce cell apoptosis. The present invention also provides methods of preparing such compounds and compositions, and methods of making and using the same.

  一般来说，本发明提供了可抑制细胞增殖和/或诱导细胞凋亡的新型喹诺酮化合物及其药物组合物。本发明还提供了制备此类化合物和组合物的方法，以及制造和使用此类化合物和组合物的方法。
• Design, Structure−Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors
  作者：Paul A. Renhowe、Sabina Pecchi、Cynthia M. Shafer、Timothy D. Machajewski、Elisa M. Jazan、Clarke Taylor、William Antonios-McCrea、Christopher M. McBride、Kelly Frazier、Marion Wiesmann、Gena R. Lapointe、Paul H. Feucht、Robert L. Warne、Carla C. Heise、Daniel Menezes、Kimberly Aardalen、Helen Ye、Molly He、Vincent Le、Jayesh Vora、Johanna M. Jansen、Mary Ellen Wernette-Hammond、Alex L. Harris

  DOI：10.1021/jm800790t

  日期：2009.1.22

  The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TK1258), are reversible ATP-competitive inhibitors of VEGFR-2, FGFR-1, and PDGFR beta with IC50 values <0.1 mu M. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.