ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate | 126824-19-9

• 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: ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate；ethyl 2-(4-methoxyphenyl)-3H-benzimidazole-5-carboxylate
• CAS: 126824-19-9
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: INNCDPZHKVKFCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到[2-(4-甲氧基苯基)-3H-苯并咪唑-5-基]甲醇
  参考文献：
  名称：

  Tris-benzimidazole derivatives: design, synthesis and DNA sequence recognition

  摘要：

  Two tris-benzimidazole derivatives have been designed and synthesized based on the known structures of the bis-benzimidazole stain Hoechst 33258 complexed to short oligonucleotide duplexes derived from single crystal X-ray studies and from NMR. In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent. Whereas one tris-benzimidazole carries a N-methyl-piperazine at the 6-position, the other one has this group replaced by a 2-amino-pyrrolidine ring. This latter substituent results in stronger DNA binding. The optimized synthesis of the drugs is described. The two tris-benzimidazoles exhibit high AT-base pair (bp) selectivity evident in footprinting experiments which show that five to six base pairs are protected by the tris-benzimidazoles as compared to four to five protected by the bis-benzimidazoles. The tris-benzimidazoles bind well to sequences like 5-TAAAC, 5'-TTTAC and 5'-TTTAT, but it is also evident that they can bind weakly to sequences such as 5'-TATGTT-3' where the continuity of an AT stretch is interrupted by a single G-C base pair. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00170-5
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲酸乙酯 在 sodium hydrogensulfite 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Discovery of a potent and highly fluorescent sirtuin inhibitor

  摘要：

  一种高度荧光的去乙酰化酶抑制剂被发现对多种癌细胞系具有生长抑制作用。

  DOI：

  10.1039/c5md00307e

文献信息

• Discovery of a potent and highly fluorescent sirtuin inhibitor
  作者：Y. K. Yoon、M. A. Ali、A. C. Wei、T. S. Choon、A. N. Shirazi、K. Parang

  DOI：10.1039/c5md00307e

  日期：——

  Highly fluorescent sirtuin inhibitor was discovered to possess growth inhibitory effect against multiple cancer cell lines.

  一种高度荧光的去乙酰化酶抑制剂被发现对多种癌细胞系具有生长抑制作用。
• Synthesis and Crystal Structures of Ethyl 2-(4-Methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate Dihydrate and Its Building Block 4-Fluoro-3-nitrobenzoic Acid
  作者：Keng Yoon Yeong、Tze Shyang Chia、Ching Kheng Quah、Soo Choon Tan

  DOI：10.1007/s10870-018-0725-3

  日期：2018.12

  The title compound, ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate (5), was synthesized and its crystal structure was studied by single-crystal X-ray diffraction technique. Compound 5 is crystallized in the centrosymmetric triclinic space group $$P\bar 1}$$ with Z = 4 and Z′ = 2, and unit-cell parameters of a = 8.9190 (3) Å, b = 12.6888 (4) Å, c = 14.7111 (5) Å, α = 98.4855 (10)°, β = 101.6379 (9)°, γ = 95.4346 (10)° and V = 1599.43 (9) Å3. Its starting material, 4-fluoro-3-nitrobenzoic acid (1), is crystallized in the non-centrosymmetric monoclinic space group P21 and Z = 4 with unit-cell parameters of a = 3.7170 (4) Å, b = 12.6475 (13) Å, c = 15.5237 (15) Å, α = 90°, β = 91.9786 (16)°, γ = 90° and V = 729.35 (13) Å3. It was noted that strong hydrogen bonds play important roles in the crystal packing of both compounds, especially in 5, in which the co-crystallized water molecules act as both strong hydrogen bond donor and strong hydrogen bond acceptor. Two molecule of compound 5 crystallized in a non symmetrical manner with four co-crystallized water molecules which play an important role in the crystal packing as strong hydrogen-bond donors.

  合成了标题化合物 2-(4-甲氧基苯基)-1H-苯并[d]咪唑-5-羧酸乙酯二水合物（5），并利用单晶 X 射线衍射技术研究了其晶体结构。化合物 5 在中心对称的三菱空间群 $$P\bar 1}$$中结晶，Z = 4，Z′ = 2，单位晶胞参数为 a = 8.9190 (3) Å, b = 12.6888 (4) Å, c = 14.7111 (5) Å, α = 98.4855 (10)°, β = 101.6379 (9)°, γ = 95.4346 (10)° 和 V = 1599.43 (9) Å3.其起始材料 4-氟-3-硝基苯甲酸 (1) 在非中心对称单斜空间群 P21 和 Z = 4 中结晶，单位晶胞参数为 a = 3.7170 (4) Å、b = 12.6475 (13) Å、c = 15.5237 (15) Å、α = 90°、β = 91.9786 (16)°、γ = 90°和 V = 729.35 (13) Å3。研究发现，强氢键在这两种化合物的晶体堆积中起着重要作用，尤其是在 5 号化合物中，共晶体水分子既是强氢键的供体，又是强氢键的受体。化合物 5 的两个分子以非对称方式结晶，其中有四个共结晶水分子，它们作为强氢键供体在晶体堆积中发挥了重要作用。
• Benzimidazole-oxindole hybrids as multi-kinase inhibitors targeting melanoma
  作者：Rasha M. Allam、Ahmed M. El Kerdawy、Ahmed E. Gouda、Kawkab A. Ahmed、Heba T. Abdel-Mohsen

  DOI：10.1016/j.bioorg.2024.107243

  日期：2024.5

  significant growth inhibition in diverse cancer cell lines. Compound stood out with a GI range of 1.23 – 3.38 µM on melanoma cell lines. Encouraged by its efficacy, it was further investigated for its antitumor activity and mechanism of action, using sorafenib as a reference standard. The hybrid compound exhibited potent cellular-level suppression of BRAF, VEGFR-2, and FGFR-1 in A375 cell line, surpassing

  在当前的研究中，设计并合成了一系列苯并咪唑-羟吲哚缀合物作为II型多激酶抑制剂。它们在 10 µM 浓度下对 BRAF 表现出中度至强效的抑制活性，高达 99.61%。值得注意的是，化合物 和 表现出最有希望的活性，抑制率为 99.44% 至 99.61%。进一步的评估表明，对激酶 BRAF、VEGFR-2 和 FGFR-1 表现出中度至强效的抑制作用。此外，NCI 对化合物的细胞毒性进行了筛选，一些化合物在不同的癌细胞系中表现出显着的生长抑制作用。该化合物在黑色素瘤细胞系上的 GI 范围为 1.23 – 3.38 µM。受其功效的鼓舞，以索拉非尼为参考标准，进一步研究其抗肿瘤活性和作用机制。该混合化合物在 A375 细胞系中表现出对 BRAF、VEGFR-2 和 FGFR-1 的有效细胞水平抑制，超过了索拉非尼的效果。研究表明，显着抑制小鼠 B16F10 肿瘤的生长，从而提高存活率和组织
• Yadagiri, Bathini; Lown, J. William, Synthetic Communications, 1990, vol. 20, # 7, p. 955 - 963
  作者：Yadagiri, Bathini、Lown, J. William

  DOI：——

  日期：——
• Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Tan Soo Choon、Rusli Ismail

  DOI：10.1016/j.ejmech.2013.06.025

  日期：2015.3

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.