Synthesis and In Vitro Antiproliferative Activity of 11-Substituted Neocryptolepines with a Branched ω-Aminoalkylamino Chain
AbstractNeocryptolepine, which is a kind of tetracyclic indoloquinoline alkaloid, exhibits the inhibition of topoisomerase II and shows antiproliferative activity. The present study describes the synthesis and antiproliferative evaluation of several neocryptolepine analogues carrying a branched, functionalized dibasic side chain at C11. These 2-substituted 5-methyl-indolo[2,3-b]quinoline derivatives were prepared by nucleophilic aromatic substitution (SNAr) of 11-chloroneocryptolepines with appropriate 1,2- and 1,3-diamines. Some of the 11-(ω-aminoalkylamino) derivatives were further transformed into 11-ureido and thioureido analogues. Many of the prepared neocryptolepine derivatives showed submicromolar antiproliferative activity against the human leukemia MV4-11 cell line. Among them, 11-(3-amino-2-hydroxy)propylamino derivatives 2h and 2k were the most cytotoxic with a mean IC50 value of 0.042 μM and 0.057 μM against the MV4-11 cell line, 0.197 μM and 0.1988 μM against the A549 cell line, and 0.138 μM and 0.117 μM against the BALB/3T3 cell line, respectively. View Full-Text
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Shaban, E.; Świtalska, M.; Wang, L.; Wang, N.; Xiu, F.; Hayashi, I.; Ngoc, T.A.; Nagae, S.; El-Ghlban, S.; Shimoda, S.; Gokha, A.A.A.E.; Sayed, I.E.T.E.; Wietrzyk, J.; Inokuchi, T. Synthesis and In Vitro Antiproliferative Activity of 11-Substituted Neocryptolepines with a Branched ω-Aminoalkylamino Chain. Molecules 2017, 22, 1954.
Shaban E, Świtalska M, Wang L, Wang N, Xiu F, Hayashi I, Ngoc TA, Nagae S, El-Ghlban S, Shimoda S, Gokha AAAE, Sayed IETE, Wietrzyk J, Inokuchi T. Synthesis and In Vitro Antiproliferative Activity of 11-Substituted Neocryptolepines with a Branched ω-Aminoalkylamino Chain. Molecules. 2017; 22(11):1954.Chicago/Turabian Style
Shaban, Elkhabiry; Świtalska, Marta; Wang, Li; Wang, Ning; Xiu, Fan; Hayashi, Ikuya; Ngoc, Tran Anh; Nagae, Sachie; El-Ghlban, Samah; Shimoda, Shiho; Gokha, Ahmed Abdel Aleem El; Sayed, Ibrahim El Tantawy El; Wietrzyk, Joanna; Inokuchi, Tsutomu. 2017. "Synthesis and In Vitro Antiproliferative Activity of 11-Substituted Neocryptolepines with a Branched ω-Aminoalkylamino Chain." Molecules 22, no. 11: 1954.
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