Материалы II студенческой межфакультетсткой конференции первокурсников по биоорганической химии
INDOLE AND ITS DERIVATIVES Andrew Brian Amoah-Danful, group 2. Scientific adviser is Tishakova Tatyana
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- Benzimidazole
INDOLE AND ITS DERIVATIVESAndrew Brian Amoah-Danful, group 2. Scientific adviser is Tishakova Tatyana.Indole (also Benzopyrrole), C8H7N, is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo dye with oleum. Indole is a colourless solid having a pleasant fragrance in highly dilute solutions. It melts at 52.5° C (126.5° F). It occurs in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan ,an essential amino acid, serotonin,a neurotransmitter, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings. It is also a precursor to many pharmaceuticals. Indole is biosynthesized via anthranilate. It condenses with serine via Michael addition of indole to PLP-aminoacrylate. Indole is a major constituent of coal-tar, and the 220–260 °C distillation fraction is the main industrial source of the material. Indole and its derivatives can also be synthesized by a variety of methods. The main industrial routes start from aniline via vapor-phase reaction with ethylene glycol in the presence of catalysts. Other precursors to indole include formyltoluidine, 2-ethylaniline, and 2-(2-nitrophenyl) ethanol, all of which undergo cyclizations. Many other methods have been developed that are applicable such as Leimgruber-Batcho indole synthesis and Fischer indole synthesis. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families. Psilocin, psilocybin, reserpine, and strychnine belong to this group. Indoles are used in anticancer (e.g.Vincristine), antiemetic (e.g. Tropisetron), anti-leukamic (e.g.Panobinostat), Schizophrenic (e.g. Roxindole) and anti-asthmatic drugs (e.g. Zafirlukast). BenzimidazoleEmmanuel Nketia, group 2. Scientific adviser is Tishakova Tatyana.Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. Heterocyclic compounds are occupied prominent place among various class of aromatic organic compounds. Benzimidazole are having a variety of therapeutic uses including antitumor, antifungal, antiparasitic, analgesics, antiviral, antihistamine, as well as use in cardiovascular disease, neurology, endocrinology, and ophthalmology. Benzimidazole moieties are a very important class of heterocyclic compounds that have many applications in pharmaceutical chemistry. Nowadays is a moiety of choice which possesses many pharmacological properties. The most prominent benzimidazole compound in nature is N-ribosyl-dimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin B12. In 1991 benzimidazole derivatives were synthesized by derivatization at N-H of benzimidazole by electron donating group and substitution with long chain of propyl, acetamido, thio, thiazole-amino, tetramethyl piperidine on pyridine resulting in good antiulcer activity . Based on their broad biological functions, they are used in clinical medicine as anti-ulcer, anti-tumor and anti-viral agents . Nowadays Infectious microbial diseases are causing problems world-wide, because of resistance to number of antimicrobial agents (β-lactam antibiotics, macrolides, quinolones, and vancomycin). A variety of clinically significant species of microorganisms has become an important health problem globally. One way to fight with this challenge is the appropriate usage of the available marketed antibiotics the other is the development of novel anti-microbial agents[5]. Hence, there will always be a vital need to discover new chemotherapeutic agents to overcome the emergence of resistance and ideally shorten the duration of therapy. Due to the structural similarity to purine, antibacterial ability of benzimidazoles are explained by their competition with purines resulting in inhibition of the synthesis of bacterial nucleic acids and proteins [6,7].
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