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A facile and high-yielding synthesis of the hydrophobic and the hexane soluble H-cardanol incorporated C(3)-aminoisoindolinones has been successfully achieved. Additionally, the synthesis of the H-cardanol embedded tetracyclic C(3)-aminoisoindolinones has also been successfully achieved. The H-cardanol incorporated isoindolinones are low melting, lipophilic solids and readily soluble in hydrocarbon solvents - a property useful for topical administration of medicinal drugs. The UV-Vis spectra of the C(3)-aminoisoindolinones with two H-cardanol units do not indicate an intramolecular association between the two aromatic rings. [ABSTRACT FROM AUTHOR]

A simple, rapid and conceptually new efficient protocol for the synthesis of 4,5‐dihydro‐1H‐benzo[g]indazole derivatives from novel enaminones prepared via Blaise reaction under catalyst free conditions is reported involving polyethylene glycol (PEG‐400) as an efficient recyclable medium without using any organic co‐solvent or additive by Microwave irridation with 91–95 % yields without chromatography. [ABSTRACT FROM AUTHOR]

The C(4) N‐heteroaryl 2‐amino‐3‐nitro‐4H‐chromenes are podophyllotoxin (POD) mimics as they possess the pharmacophore features of the anticancer natural product. We have achieved a facile synthesis of several such 4H‐chromenes by substitution of C(4) SMe in N‐alkyl 4‐(methylthio)‐3‐nitro‐4H‐chromen‐2‐amines with heteroaromatic amines like 2‐aminopyridines and 2‐aminopyrimidines. Resulting 4H‐chromenes were evaluated for anticancer activity against prostate and lung cancer cell lines. Two of the 4H‐chromenes showed significant anti‐cancer activity, even better than POD. Both of them were non‐toxic towards normal cell‐lines. In silico ADMET studies revealed drug‐likeliness of all the 4H‐chromenes. Molecular docking studies with αβ tubulin concurred with in vivo results and revealed that the 4H‐chromenes bind to the active site of POD. Molecular dynamics simulation studies on the complexes of αβ tubulin with the two best 4H‐chromenes revealed high stability. Overall, our studies revealed that the two 4H‐chromenes could act as lead compounds for further development of potent anticancer drugs. All the newly synthesized 4H‐chromenes were subjected to in vivo anti‐cancer activity against prostate and lung cancer cell lines. The studies revealed that two of them 18 q and 18 s exhibited IC50values better than POD. [ABSTRACT FROM AUTHOR]

Copper(II) trifluoromethanesulfonate (Cu(OTf)2) efficiently catalyzes the C-C coupling of 3-hydoxyisoindolinones with a variety of aryl-, heteroaryl-, and alkenylboronic acids to furnish C(3) aryl-, heteroaryl-, and alkenyl-substituted isoindolinones. The coupling reactions work smoothly in 1,2-dicholoroethane (DCE) reflux, to effect both inter- and intramolecular versions. This is the first report on C(sp³)-OH cleavage with concomitant C-C coupling. The photolabile 2-nitrobenzyl protecting group is most appropriate for promotion of the coupling reaction and for deprotection. The tetracyclic ring motif of the alkaloid neuvamine was prepared by applying the newly developed copper-catalyzed C-C coupling. [ABSTRACT FROM AUTHOR]

An effective synthesis of highly functionalized 3-nitrothiophenes was achieved from the reaction of simple, inexpensive, and readily available dipotassium 2-nitro-1,1 -ethylyenedithiolate with a-chloromethyl ketones in toluene catalyzed by tetrabutylammonium bromide (TBAB). Thiophene formation is highly Sensitive and selective for chlorine, present as a leaving group in α-chloromethyl ketones. [ABSTRACT FROM AUTHOR]