Complexation Studies Of Crown Ethers With Alkali Metal Cations In Methanol. [QD474. Y46 2004 f rb].

Tindak balas pengalkilan di antara dibenzo-15-mahkota-5 (DB15C5) dengan t-butanol dalam asid trifluoroasetik akan memberi 2,3,8,9-(4’,4”-di-tert-butil)-dibenzo-1,4,7,10,13-pentaoksasiklopentadeka-2,8-diena (t2-DB15C5). The alkylation reaction between dibenzo-15-crown-5 (DB15C5) and t-butyl alcohol in trifluoroacetic acid yielded 2,3,8,9-(4’,4”-di-tert-butyl)-dibenzo-1,4,7,10,13-pentaoxacyclopentadeca-2,8-diene (t2-DB15C5)

Synthesis And Biological Activity Of Benzimidazole Analogs As Sirtuin Enzyme Inhibitors

Bagi mencari perencat enzim sirtuin yang poten, 90 analog benzimidazol telah berjaya direka.Kaedah sintesis yang digunakan dalam projek ini mengambilkira langkah-langkah yang lestari.Sebatian4h (ethyl 2-(4-(piperidin-1-yl)phenyl)-1H-benzo[d]imidazole-5-carboxylate)merupakanperencat enzim sirtuin yang paling baik dalam projek ini. Ia didapati merencat sirtuin-2 (SIRT2) lebih baik daripada sirtuin-1 (SIRT1). Daripada profil sebatian dengan aktiviti perencatan SIRT1/SIRT2, perhubungan struktur dengan aktiviti boleh disimpulkan.Juga menarik perhatian ialah kemampuan sebatian4h untuk mengekang pertumbuhan sel kanser kolorektal. Selain daripada itu, ia juga mempunyai keupayaan untuk mencegah pertumbuhan sel kanser leukemia dan payudara. Pemodelan komputer turut digunakan untuk memberi penjelasan yang wajar terhadapkeputusan aktiviti yang diperolehi. Sebatian4h didapati boleh didokkan kedalam tapak aktif enzim SIRT2 dengan menggunakan struktur kristal (PDB: 3ZGV). In the effort to search for potent sirtuin inhibitors, 90 benzimidazole analogs across 6 series were designed, synthesized and characterized. Compound 4h (ethyl 2-(4-(piperidin-1-yl)phenyl)-1H-benzo[d]imidazole-5-carboxylate)was identified to be the most potent sirtuin inhibitor in this project with a preference for sirtuin-2 (SIRT2) inhibition over SIRT1. Based on the profile of the compounds along with their demonstrated SIRT1/SIRT2 inhibitory activities, a structure-activity-relationship was deduced for the benzimidazole moeity. Remarkably, compound 4h exhibited potent growth inhibitory effect on colorectal cancer cell lines. Apart from colorectal cancer, it was also found to possess antiproliferative activity against leukemia and breast cancer cell lines. Molecular docking approach was used to rationalize the observed activity. The SIRT2 crystal homology model (PDB: 3ZGV) was found to be able to accommodate compound 4h in its active site, thus supporting the notion that 4h was indeed able to strongly inhibit the SIRT2 activity

Ethyl 4-anilino-3-nitro­benzoate

In the title compound, C15H14N2O4, the dihedral angle between the benzene and phenyl rings is 73.20 (6)°. An intra­molecular N—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into a layer parallel to the bc plane

Ethyl 2-(4-chloro­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate

In the title compound, C22H17ClN2O2, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, mol­ecules are linked into a zigzag chain along the a axis by inter­molecular C—H⋯O hydrogen bonds. C—H⋯π inter­actions are also present

Ethyl 2-(4-bromo­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate

In the title compound, C22H17BrN2O2, the benzimidazole ring system is essentially planar, with a maximum deviation of 0.017 (1) Å, and forms dihedral angles of 27.79 (6) and 64.43 (6)° with the phenyl and bromo-substituted benzene rings, respectively. In the crystal, mol­ecules are linked into one-dimensional chains along the a axis by weak C—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯π inter­actions are also present

Ethyl 1-phenyl-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimidazole-5-carboxyl­ate

The asymmetric unit of the title compound, C23H17F3N2O2, contains two mol­ecules. In one of the mol­ecules, the phenyl and triflouromethyl-substituted benzene rings form dihedral angles of 52.05 (8) and 33.70 (8)°, respectively, with the benzimidazole ring system, while the dihedral angle between them is 58.24 (10)°. The corresponding values in the other mol­ecule are 58.40 (8), 25.90 (8) and 60.83 (10)°, respectively. In the crystal, mol­ecules are linked into chains along [100] by C—H⋯O and C—H⋯N hydrogen bonds. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.6700 (12) Å] also occur

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benz­imidazole-5-carboxyl­ate

In the title compound, C24H25N3O5, the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methyl­ene C atoms forming the flap. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal packing is further stabillized by weak π–π inter­actions between the benzene rings within the benzimidazole ring system [centroid–centroid distance = 3.7955 (7) Å]. A weak C—H⋯π inter­action involving the benzodioxole ring is also present

Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

In the title compound, C22H21BrN4O2·H2O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1) and 0.002 (1) Å], and form a dihedral angle of 73.46 (9)°. The dihedral angle between the benzene rings is 29.33 (7)°. In the crystal, mol­ecules are connected via C—H⋯O and O—H⋯N hydrogen bonds, forming layers in the ab plane

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

In the title compound, C23H22N4O4, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methyl­ene C atom at the flap. In the crystal, C—H⋯O and C—H⋯N inter­actions link the mol­ecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π–π stacking inter­actions [centroid–centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C—H⋯π inter­actions