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Direct Nucleophilic Attack/Addition Cyclization and C–H Bond Activation Reactions to Synthesize 3-Benzyl-/3-Benzyl-2-phenyl-benzo[4,5]imidazo[2,1-b]thiazoles

ABSTRACT:

SUBMITTER: Wang D

PROVIDER: S-EPMC10702324 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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C(sp2)-H selenylation of substituted benzo[4,5]imidazo[2,1-b]thiazoles using phenyliodine(iii)bis(trifluoroacetate) as a mediator.

Project description:Herein, an expeditious metal-free regioselective C-H selenylation of substituted benzo[4,5]imidazo[2,1-b]thiazole derivatives was devised to synthesize structurally orchestrated selenoethers with good to excellent yields. This PIFA [bis(trifluoroacetoxy)iodobenzene]-mediated protocol operates under mild conditions and offers broad functional group tolerance. In-depth mechanistic investigation supports the involvement of radical pathways. Furthermore, the synthetic utility of this methodology is portrayed through gram-scale synthesis.

| S-EPMC10835571 | biostudies-literature

Crystal structures of methyl 3-phenyl-4,5-di-hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl-ate and methyl 1-methyl-3-phenyl-4,5-di-hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl-ate.

Project description:The title compounds, C19H18N2O3, (I), and C20H20N2O3, (II), differ only by a methyl substituent on the seven-membered oxazepine ring in (II). In both compounds, these rings have a twist-chair conformation. The phenyl ring makes a dihedral angle of 73.42 (10)° with the benzimidazole ring system mean plane (r.m.s. deviation = 0.015 Å) in (I) and 83.07 (7)° in (II) (r.m.s. deviation = 0.026 Å). The methyl carboxyl-ate groups are planar to within 0.031 (2) in (I) and 0.003 (2) Å in (II). They are inclined to the phenyl and benzimidazole ring system by 33.78 (16) and 87.56 (14)°, respectively, in (I) and by 53.04 (12) and 60.22 (11)°, respectively, in (II). In the crystal of (I), mol-ecules stack in a herringbone fashion and are linked by C-H⋯O hydrogen bonds, forming chains along [100]. In the crystal of (II), there are no significant inter-molecular inter-actions present.

| S-EPMC4257324 | biostudies-literature

8H-Chromeno[2',3':4,5]imidazo[2,1-a]isoquinoline.

Project description:The title compound, C(18)H(12)N(2)O, comprises two aromatic fragments, viz., imidazo[2,1-a]isoquinoline and benzene, linked by oxygen and methyl-ene bridges. Despite the absence of a common conjugative system within the mol-ecule, it adopts an essentially planar conformation with an r.m.s. deviation of 0. 036 Å. In the crystal, due to this structure, mol-ecules form stacks along the b axis by π⋯π stacking inter-actions, with shortest C⋯C distances in the range 3.340 (4)-3.510 (4) Å. The mol-ecules are bound by inter-molecular C-H⋯O inter-actions within the stacks and C-H⋯π inter-actions between the stacks.

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9,10-Dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one.

Project description:In the title compound, C(14)H(10)N(2)O, all non-H atoms are essentially coplanar (r.m.s. deviation = 0.013 Å). The crystal structure is stabilized by π-π stacking inter-actions [centroid-centroid distance = 3.506 (3) Å].

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7-Nitro-2-phenyl-imidazo[2,1-b][1,3]benzo-thia-zole.

Project description:In the title mol-ecule, C15H9N3O2S, the central imidazo[2,1-b][1,3]benzo-thia-zole heterotricyclic unit is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring and nitro group are twisted by 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the heterotricycle. In the crystal, mol-ecules are linked by π-π stacking inter-actions into columns along [100]; the inter-planar distance between neighboring imidazo[2,1-b][1,3]benzo-thia-zole planes within the columns is 3.370 (2) Å. Furthermore, the columns interact with each other by secondary S⋯O [2.9922 (10) and 3.1988 (11) Å] inter-actions, forming a three-dimensional framework.

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2-Phenyl-5,6,7,8-tetra-hydro-imidazo[2,1-b][1,3]benzo-thia-zole.

Project description:The title compound, C15H14N2S, crystallizes with two independent mol-ecules in the asymmetric unit. The central imidazo[2,1-b][1,3]benzo-thia-zole unit is planar (r.m.s. deviations of 0.010 and 0.008 Å for the two independent mol-ecules). The fused tetra-hydro-hexane ring adopts a half-chair conformation. The phenyl substituent is twisted by 16.96 (13) and 22.89 (12)° relative to the central imidazo[2,1-b][1,3]benzo-thia-zole unit in the two mol-ecules. In the crystal, there are no significant intermolecular interactions present.

| S-EPMC4051062 | biostudies-literature

Synthesis, Characterization, and Biological Activity of a Novel Series of Benzo[4,5]imidazo[2,1-b]thiazole Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors.

Project description:Based on the analysis of epidermal growth factor receptor (EGFR) complexes with gefitinib with molecular docking, the scaffold-hopping strategy, combination of the active substructures, and structural optimization of EGFR inhibitors, a novel series of benzo[4,5]imidazo[2,1-b]thiazole derivatives was designed, synthesized, and evaluated for antitumor activity in human cancer cell lines and cellular toxicity against human normal cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay and EGFR inhibitory activities in vitro. Some target compounds such as 2-(benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N-(2-hydroxyphenyl)acetamide (D04) and 2-(benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N-(naphthalen-1-yl)acetamide (D08) have shown significant antitumor activity against the EGFR high-expressed human cell line HeLa. All the target compounds showed hardly any antitumor activity against the EGFR low-expressed human cell line HepG2, and nearly no cellular toxicity against the human normal cell lines HL7702 and human umbilical vein endothelial cell lines (HUVEC). The inhibitory activities against EGFR kinase in vitro of the three target compounds were greatly consistent with the anti-proliferative activities. The preliminary structure⁻activity relationships of the target compounds were summarized. Conclusively, the novel benzo[4,5]imidazo[2,1-b]thiazole derivatives as novel potential EGFR inhibitors may be used as the potential lead compounds for the development of antitumor agents.

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Using Imidazo[2,1-b][1,3,4]thiadiazol Skeleton to Design and Synthesize Novel MNK Inhibitors.

Project description:Mitogen-activated protein kinase-interacting protein kinases (MNKs) phosphorylate eukaryotic initiation factor 4E (eIF4E) and regulate the processes of cell proliferation, cell cycle, and migration and invasion of cancer cells. Selectively inhibiting the activity of MNKs could be effective in treating cancers. In this study, we report a series of novel MNK inhibitors with an imidazo[2,1-b][1,3,4]thiadiazol scaffold, from which, compound 18 inhibited the phosphorylation of eIF4E in various cancer cell lines potently. Compound 18 was more potent against MNK2 than MNK1, and decreased the levels of cyclin-B1, cyclin-D3, and MMP-3 in A549 and MDA-MB-231 cells, impaired cell growth and colony formation, arrested the cell cycle in the G0/G1 phase, and inhibited cell migration and the secretion of TNF-α, MCP-1, and IL-8 from A549 cells. It represents a starting compound to design further inhibitors that selectively target MNKs and apply in other diseases.

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Synthesis of Benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization.

Project description:2-(2-Bromovinyl)benzimidazoles and 2-(2-bromophenyl)benzimidazoles react with cyanamide by microwave irradiation in dimethylformamide in the presence of a catalytic amount of CuI along with a base to give the corresponding benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and benzo[4,5]imidazo[1,2-c]quinazolin-6-amines, respectively, in moderate to good yields. 2-(2-Bromophenyl)indoles also react with cyanamide under similar conditions to afford indolo[1,2-c]quinazolin-6-amines. The reaction pathway seems to proceed via a sequence such as intermolecular C-N coupling, C-N formative cyclization, and tautomerization.

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4-Benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine.

Project description:The imidazopyridine fused ring in the title compound, C(19)H(14)BrN(3), is almost coplanar with the phenyl ring at the 2-position of the five-membered ring [dihedral angle = 2.4 (1). The crystal structure features short Br⋯Br contacts [3.562 (1) Å].

| S-EPMC2983780 | biostudies-literature

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