Transition metals in organic synthesis - Part 83#: Synthesis and pharmacological potential of carbazoles

Abstract

A series of carbazole derivatives with promising pharmacological properties has been prepared using either an iron-mediated or a palladium-catalyzed synthetic approach. The carbazole alkaloids carbazoquinocin C, carbazomadurin A and B, epocarbazolin A and B, neocarazostatin B, and carquinostatin A are antioxidants acting as free-radical scavengers. Thus, they represent potential lead compounds for the development of novel drugs against diseases initiated by oxygenderived free radicals. Initiated by the first naturally occurring carbazole alkaloids with antituberculosis (anti-TB) activity, clausine K and micromeline, a study on the structure-activity relationships for anti-TB-active carbazole derivatives has been carried out. The 6-oxygenated carbazoles glycozoline and glycozolinine show antibiotic activity towards several microorganisms. The 7-oxygenated carbazole siamenol exhibits anti-HIV activity.

A New Alkaloid from the Aerial Parts of Bupleurum chinense DC.

“…Compound 2 could suppressed hind paw swelling in the adjuvant‐arthritic rat model, while also having antioxidant, anti‐neuroinflammatory, anti‐inflammatory, anti‐inflammatory, anti‐inflammatory and antiviral effects . Antimycobacterial potency against the Mycobacterium tuberculosis strain H37Rv and impressive anti‐inflammatory activity were reported for compounds 3 . Compound 4 was found to be active against rat lens aldose reductase which displayed antidiabetic property .…”

“…[12][13][14][15] Antimycobacterial potency against the Mycobacterium tuberculosis strain H37Rv and impressive anti-inflammatory activity were reported for compounds 3. [16,17] Compound 4 was found to be active against rat lens aldose reductase which displayed antidiabetic property. [18] Thymine (6) was a key intermediate in the synthesis of the anti-AIDS drug AZT (Zidovudine) and other related drugs, which was obtained by methylating uracil (5).…”

Total synthesis of biologically active alkaloids using transition metals

“…A special focus has been on the antibiotic properties and the inhibition of Mycobacterium tuberculosis exhibited by some carbazole derivatives [64][65][66][67]. In the course of our project, several total syntheses of carbazole alkaloids with a variety of structures have been completed over the last four years (Fig.…”

Transition Metals in Organic Synthesis, Part 87: An Efficient Palladium-­Catalyzed Route to 2-Oxygenated and 2,7-Dioxygenated Carbazole Alkaloids - Total Synthesis of 2-Methoxy-3-methylcarbazole, Glycosinine, Clausine L, Mukonidine, and Clausine V

“…According to our recent findings, 34 the carbazoles described above could be of interest due to their potential as anti-TB agents.…”