Benzimidazolate derivatives

Pharmacological activity spectrum and toxicological properties of benzimidazole derivatives 99KFZ(5)6. 

Fig. 3.10 Recognition of the DNA minor groove with benzimidazole derivatives, (a) Structure of the dimeric core for Py-benzimi-dazole (Bi), Py-hydroxybenzimidazole (Hz) and Py-imidazopyridine (Ip) (left) in comparison with the five-membered ring system (right). H-bonding surfaces along the recogni-...

Three different microwave-assisted synthetic routes to benzimidazole derivatives are summarized in Scheme 6.205, involving the condensation of 1,2-phenylenedi-amines with either carboxylic acids (Scheme 6.205 a and b) [368, 369] or two equivalents of aldehydes (Scheme 6.205 c) [370], or by cyclization of N-acylated-diamino-pyrimidines mediated by a strong base (Scheme 6.205 d and e) [371, 372],... 

Benzimidazole derivatives are excellent antioxidants, with limited fatigue activity. They offer excellent metal poison protection. 

The reactions of 2-(2-benzylaminophenyl)benzimidazole derivatives 247 with electrophilic 7-chloro-4,6-dinitro-benzofuroxan afforded a new bipolar spiro-rr-complex 248. The structure of the complex was established by X-ray diffraction analysis (Equation 48) <2002CHE1428, 2004RCB2075>. 

Thiabendazole, a benzimidazole derivative, is an antihelminthic drug used primarily to treat infections caused by... 

Ruthenium-catalyzed carbonylations of a variety of heterocycles have been disclosed. With benzimidazole derivatives, the regioselectivity changes upon introduction of a C(2) substituent (Equations (107) and (108)).100... 

With dichloromaleimides. A similar cyclization of 2-mercaptobenzoimidazole with an appropriate dichloromaleimide as key reagent gave thiazolo[3,2- ]benzimidazole derivatives 406 (Equation 184) <2001H(55)2189>. 

Diethyl N-(4-Aminophenyl)aminomethylenemalonate (167, R = H) was reacted with N, Af -bis(methoxycarbonyl)-5-methylisothiourea in the presence of p-toluenesulfonic acid in boiling methanol for 4 hr to afford the guanidine derivative (1590) in 50% yield. The guanidine (1590) was oxidized in chloroform with lead tetraacetate to the quinoline diimine (1591), which cyclized to 1592. After methanolysis, the 2-(methoxycarbon-ylamino)benzimidazole derivative (1593) was obtained in 41% yield [86JCR(S)161]. 

Benzimidazole is an important heterocyclic nucleus in the field of medicinal chemistry. The most prominent benzimidazole compound in nature is N-ribosyldimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin B12. The versatile nature of benzimidazole makes it a highly explored molecule in medicinal chemistry. A number of pharmacological activities are associated with benzimidazole derivatives such as anthelmintic, antiulcer, antipsychotic, proton pump inhibitor, antianxiety, anti-emetic and sedative, vasodilator, anticancer, analgesic, antihistaminic, antifungal, antiviral and antimicrobial. 

In the latter case the structure was established by reduction with stannous chloride in acetic acid, which afforded the imidazole derivative (104), thus proving ortho substitution, followed by comparison of the ultraviolet spectrum of 104 with the two possible benzimidazole derivatives of carbazole. Deamination of 103 via diazotization in sulfuric acid afforded 1-nitrodibenzothiophene (105) (54%), being the only recorded route to this compound (Scheme 5). Initial attempts to hydrolyze 102 to the nitroamine (103) had been made with ethanolic hydrogen chloride... 

Fig. 29 Synthesis of benzimidazole derivative from aromatic 1,2-diamines...

AntihBiminticS Flubendazole was launched as an antihelmintic. It seems to have a mode of action close to that of benzimidazole derivatives used as antihelmintics mebendazole, albendazole), which are reported to block the capture of glucose by the parasite (Figure 8.23). 

Mechanism of Action A synthetic benzimidazole derivative that degrades parasite cytoplasmic microtubules and irreversibly blocks glucose uptake in helminths and larvae. Vermicidal. Therapeutic Effect Depletes glycogen, decreases ATP, causes helminth death. 

Cfiemical Class Benzimidazole derivative I Clinical Pharmacology ... 

Brand Name(s) Protonix, Protonix IV Cfiemical Class Benzimidazole derivative... 

Benzimidazol-Derivate uberdecken einen weiten u. a. verwendet als... 

---