Benzimidazoles: A biologically active compounds

A compound A) of the formula: or its pharmaceutically acceptable salt, wherein R19 is selected from: in which: each Z10, Z11, Z12 and Z13 is independently selected from N, CR20 or CR1 '; and each Z14, Z15 and Z16 is independently selected from N, NR1 ', S, O, CR20 or CR1' ', zero to two of Z10, Z11, Z12 or Z13 are N; wherein: at least one of Z14, Z15 and Z16 is N, NR1 ', O or S; zero to one of Z14, Z15 and Z16 is S or O; zero to two of Z14, Z15 and Z16 are N or NR1 '; zero to an R20 is a solubilizing group; and zero to an R1 'is optionally substituted linear or branched C1-C3 alkyl; each R20 is independently selected from H or a solubilizing group; R21 is selected from -NR1'-C (O) -, -NR1'-S (O) 2-, -NR1'-C (O) -NR1'-, -NR1'-C (S) -NR1'- , -NR1'-C (S) -NR1'-CR1'R1 '-, - NR1'-C (O) -CR1'R1'-NR1'-, -NR1'-C (> = NR1') - NR1 '-, -C (O) -NR1'-, -C (O) -NR1'-S (O) 2-, -NR1'-, -CR1'R1'-, -NR1'-C (O) - CR1 '> = CR1'-, -NR1'-S (O) 2-NR1'-, -NR1'-C (O) -NR1'-S (O) 2-, -NR1'-CR1'R1'- C (O) -NR1'-, -CR1'R1'-C (O) -NR1'-, -NR1'-C (O) -CR1 '> = CR1'-CR1'R1'-, -NR1'- C (> = N-CN) -NR1'-, -NR1'-C (O) -CR1'R1'-O-, -NR1'-C (O) -CR1'R1'-CR1'R1'-O -, -NR1'-S (O) 2-CR1'R1'-, -NR1'-S (O) 2-CR1'R1'- CR1'R1'-, -NR1'-C (O) -CR1 ' R1'-; -NR1'-C (O) -CR1'R1'-CR1'R1'-, -NR1'-C (S) -NR1'-CR1'R1'-CR1'R1'-, -NR1'-C (O )-OR-.

Sirtuin modulating compounds

Donepezil-based multi-functional cholinesterase inhibitors for treatment of Alzheimer's disease.

The current state and prospects of development of the chemistry of isomeric thienopyridines (synthesis, chemical transformations, and biological activities) are analyzed. Particular attention is given to studies published in the last 10–15 years.

Thienopyridines: synthesis, properties, and biological activity

2-Aminobenzothiazole-6-carboxylic acid ( 1 ), on condensation with chloroacetyl chloride yielded 2-(2-chloroacetylamino)benzothiazole-6-carboxylic acid ( 2 ), which on amination with hydrazine hydrate yielded in turn 2-(2-hydrazinoacetylamino)benzo-thiazole-6-carboxylic acid ( 3 ) Compound 3 , on condensation with various aromatic aldehydes afforded a series of 2-{2-[N’-(arylidene)hydrazino]acetylamino}benzothiazole-6-carboxylic acids 4a-h , which upon dehydrative annulation in the presence of chloroacetyl chloride and triethylamine yielded 2-{2-[3-chloro-2-(aryl)-4-oxoazetidin-1-ylamino]-acetylamino}benzothiazole-6-carboxylic acids 5a-h  The synthesized compounds 4a-h and 5a-h were screened for their antibacterial activity against four microorganisms: Staphylococcus aureus (Gram positive), Bacillus subtilis (Gram positive), Psuedomonas aeruginosa (Gram negative) and Escherichia coli (Gram negative) They were found to exhibit good to moderate antibacterial activity The antifungal activity of these compounds were also tested against three different fungal species None of them were active against the species tested

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Synthesis and biological activity of N-substituted-3-chloro-2-azetidinones.

The reaction of 2H-2-oxobenzo[b]pyran-3-hydrazide (2) with carbon disulfide in basic DMF afforded potassium thiocarbamate 3, which readily underwent heterocyclization upon its reaction with hydrazine and/or phenacyl bromide to yield 1,2,4-tiazole (4) and thiazole 7 derivatives, respectively. Condensation of 4 with substituted phenacyl bromide and/or chloranil gave 1,2,4-triazole[3,4-b]thiadiazine (5a,b) and 3,10-bis-[2H-2-oxobenzo[b]pyran-3-yl]-6,13-dichloro-bis-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazino[5′,6′-b:5′,6′-e]cyclohexa-1,4-diene (6), respectively. Cyclization of thiosemicarbazide 10 by refluxing it in sodium hydroxide and/or phosphoryl chloride afforded triazole 13 and thiadiazole 15 derivatives, respectively. Also, 10 reacted with phenacyl bromide in the presence of anhydrous sodium acetate to give the oxothiazolidine derivative 17. The structure of the synthesized compounds were confirmed by elemental analyses, IR, 1H NMR, and mass spectra. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:114–120, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10109

Heterocyclic synthesis containing bridgehead nitrogen atom: Synthesis of 3-[(2H)-2-oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazine and thiazole derivatives

Synthesis and reactivity of cyanomethyl 2‐amino‐4‐methylthiazolyl ketone. A facile synthesis of novel pyrazolo[5,1‐c]1,2,4‐triazine, 1,2,4‐triazolo[5,1‐c]1,2,4‐triazine, 1,2,4‐triazino[4,3‐a]benzimidazole, pyridazine‐6‐imine and 6‐oxopyridazinone derivatives

Mohamed A. Raslan

Papers

Heterocyclic synthesis containing bridgehead nitrogen atom: Synthesis of 3-[(2H)-2-oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazine and thiazole derivatives

Synthesis and reactivity of cyanomethyl 2‐amino‐4‐methylthiazolyl ketone. A facile synthesis of novel pyrazolo[5,1‐c]1,2,4‐triazine, 1,2,4‐triazolo[5,1‐c]1,2,4‐triazine, 1,2,4‐triazino[4,3‐a]benzimidazole, pyridazine‐6‐imine and 6‐oxopyridazinone derivatives

Synthesis of new pyridazin- 6-ones, pyridazin-6-imines, 4-pyridazinals, and pyridines

Synthesis of 3,3′-bi-1,2,4-Triazolo[4,5-a]- benzimidazole, 5,5′-bi-1,3,4-Thiadiazole, and Thiazolo[3,2-a]benzimidazole Derivatives

Fused Polyaza-heterocycles and 1,3,4-Thiadiazoles via A Tricyano Synthon