126824-19-9Relevant academic research and scientific papers
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
Yeong, Keng Yoon,Chia, Tze Shyang,Quah, Ching Kheng,Tan, Soo Choon
, p. 170 - 176 (2018)
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 P1 ˉ with Z = 4 and Z′ = 2, and unit-cell parameters of a = 8.9190 (3) ?, b = 12.6888 (4) ?, c = 14.7111 (5) ?, α = 98.4855 (10)°, β = 101.6379 (9)°, γ = 95.4346 (10)° and V = 1599.43 (9) ?3. 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) ?, b = 12.6475 (13) ?, c = 15.5237 (15) ?, α = 90°, β = 91.9786 (16)°, γ = 90° and V = 729.35 (13) ?3. 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. Graphical Abstract: 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. [Figure not available: see fulltext.].
Discovery of a potent and highly fluorescent sirtuin inhibitor
Yoon,Ali,Wei,Choon,Shirazi,Parang
, p. 1857 - 1863 (2015)
In search for potent sirtuin inhibitors, a series of diversified 1,2-disubstituted benzimidazole analogues were synthesized using a one-pot method. The most potent compound in the series (BZD9L1) was discovered to show high autofluorescence which can be utilized to predict its localization in cells. More importantly, BZD9L1 displayed strong antiproliferative effects against a panel of cancer cells tested. Molecular docking studies also help to explain the observed structure-activity relationship.
Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
Yoon, Yeong Keng,Ali, Mohamed Ashraf,Wei, Ang Chee,Choon, Tan Soo,Ismail, Rusli
, p. 614 - 624 (2015/03/18)
Abstract 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 1H NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain using BacTiter-Glo 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 IC50 of less than 15 μM. 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 μM.
Tris-benzimidazole derivatives: Design, synthesis and DNA sequence recognition
Ji, Yu-Hua,Bur, Daniel,H?sler, Walter,Schmitt, Valérie Runtz,Dorn, Arnulf,Bailly, Christian,Waring, Michael J.,Hochstrasser, Remo,Leupin, Werner
, p. 2905 - 2919 (2007/10/03)
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.
Convenient Routes to Substituted Benzimidazoles and Imidazolopyridines Using Nitrobenzene as Oxidant
Yadagiri, Bathini,Lown, J. William
, p. 955 - 963 (2007/10/02)
Various substituted benzimidazoles and imidazolopyridines 5a-c have been prepared by condensation of appropriate diamines and aldehydes in nitrobenzene.This method has been utilized to synthesize compounds 5f-h, which are analogues of the DNA binding fluorochrome Hoechst 33258.
