Arzel, Erwan published the artcileNew synthesis of benzo-δ-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-carbolines, benzo-δ-carbolines, and cryptolepines, Quality Control of 146140-95-6, the publication is Journal of Medicinal Chemistry (2001), 44(6), 949-960, database is CAplus and MEDLINE.
Benzo-δ-carbolines I and cryptolepines II (R = H, Me, Et, Pr, Ph) and their salts were prepared using strategies based on the association between halogen-dance and hetero-ring cross-coupling. The syntheses are fully convergent and regioselective with overall yields of 27-70%. Thus, coupling of 3-fluoro-2-iodoquinoline with the phenylboronate 2-(Me3CCONH)C6H4B(OH)2 gave the phenylquinoline III. Treatment of III with pyridinium chloride at 215° for 30 min and then with aqueous NH3 gave 83% I (R = H). A halogen-dance mechanism in the quinoline series was proposed. The formal synthesis of potential antimalarial compounds and the first total synthesis of 11-isopropylcryptolepine was described. Cytotoxic activity against mammalian cells and activities against Plasmodium falciparum and Trypanosoma cruzi of benzo-δ-carbolines and δ-carbolines were evaluated in vitro to study the structure-activity relationships. For benzo-δ-carbolines, methylation at N-5 increases the cytotoxic and antiparasitic activities. A further alkylation on C-11 generally increases the cytotoxic activity but not the antiparasitic activity, cryptolepine and 11-methylcryptolepine being the most active on both parasites. Taking advantage of the fluorescence of the indoloquinoline chromophore, cryptolepine was localized by fluorescence microscopy in parasite DNA-containing structures suggesting that these compounds act through interaction with parasite DNA as proposed for cryptolepine on melanoma cells. For δ-carbolines, methylation at N-1 is essential for the antimalarial activity. 1-Methyl-δ-carboline specifically accumulates in the intracellular parasite. It has weak cytotoxic activity and can be considered as a potential antimalarial compound
Journal of Medicinal Chemistry published new progress about 146140-95-6. 146140-95-6 belongs to amides-buliding-blocks, auxiliary class Boronic acid and ester,Amine,Benzene,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (2-Pivalamidophenyl)boronic acid, and the molecular formula is C11H16BNO3, Quality Control of 146140-95-6.
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