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Novel group of phenoxy-substituted enediyne-triazole conjugates were synthesized by Huisgen [3+2] cycloaddition reaction (Click chemistry) in aqueous media. It was observed that enediynes were stable in aqueous medium and open-air conditions.

A novel group of symmetrical and asymmetrical acyclic enediynes has been synthesized by using Sonogashira coupling conditions and characterized spectroscopically. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

Syntheses and antibacterial activity of 13-membered 1,3-phendioxy substituted cyclic enediynes are reported. The compounds were screened against gram-positive and gram-negative strains and some of the compounds exhibit potent antibacterial activity.

A convenient method for the synthesis of symmetrically and asymmetrically substituted acyclic enediynes has been developed using microwave irradiation. The reaction completes in 3-5 minutes, while same reaction takes 14-18 h to complete under conventional heating method.

A novel series of quinoline triazole amide analogues ( 38 – 51 ) has been synthesized. Analogues 38 – 44 had a Cl substituent at the 7-position of the quinoline ring, while 45 – 51 had a CN substituent at this position. Compounds 40 , 45 and 49 were found to be the most active in the series against the Plasmodium falciparum chloroquine-sensitive D10 strain, with IC 50 values in the range of 349–1247 nM, with 40 and 45 , but not 49 also exhibiting similar activity against the chloroquine-resistant K1 strain of parasite. Quinoline triazoles 40 and 44 were the most active β-haematin inhibitors, with 50% inhibitory concentrations of 14.7 and 8.9 μM respectively. In vitro antimalarial activity of the 7-Cl bearing analogues 38 – 44 exhibited a strong linear dependence of log(1/IC 50 ) on log P . Thus, the more lipophilic, the more active it was found be. The 7-CN series 45 – 51 showed no such dependence. The resistance index (IC 50 K1/IC 50 D10) also exhibited a linear dependence on log P , with a substantially steeper slope in the case of the 7-Cl series. The findings demonstrate the feasibility of producing hydrophilic analogues with strong activity and low cross-resistance with chloroquine.