Targeting tubulin polymerization by novel 7-aryl-pyrroloquinolinones: Synthesis, biological activity and SARs was written by Bortolozzi, Roberta;Mattiuzzo, Elena;Dal Pra, Matteo;Sturlese, Mattia;Moro, Stefano;Hamel, Ernest;Carta, Davide;Viola, Giampietro;Ferlin, Maria Grazia. And the article was included in European Journal of Medicinal Chemistry in 2018.Synthetic Route of C18H37Cl This article mentions the following:
For wide-ranging SARs, a series of 7-arylpyrroloquinolinones, e.g., I (R1 = Me, Ph, 1-naphthyl, 1,3-benzodioxol-5-yl, etc.; R2 = Et, n-C18H37), was synthesized through a robust procedure. For comparison with the reference 3-ethyl-7-phenyl-3H-pyrrolo[3-2-f]quinolin-9-one, the angular geometry and substituents at the 3 and 7 positions were varied to explore interactions inside the colchicine site of tubulin. Among the new compounds synthesized, potent cytotoxicity (low and sub-nanomolar GI50 values) was observed with compounds I (R1 = 1-naphthyl, 1,3-benzodioxol-5-yl; R2 = Et), both more potent than 3-ethyl-7-phenyl-3H-pyrrolo[3-2-f]quinolin-9-one, in both leukemic and solid tumor cell lines. Neither of the two above compounds I induced significant cell death in normal human lymphocytes, suggesting that these compounds may be selectively active against cancer cells. In particular, I (R1 = 1,3-benzodioxol-5-yl; R2 = Et) (II) was a potent inducer of apoptosis in the A549 and HeLa cell lines. With both compounds, induction of apoptosis was associated with dissipation of the mitochondrial transmembrane potential and production of reactive oxygen species, indicating that cells treated with these compounds followed the intrinsic pathway of apoptosis. Moreover, immunoblot anal. revealed that the compound II even at 50 nM reduced the expression of anti-apoptotic proteins such as Bcl-2 and Mcl-1. Finally, mol. docking studies of the newly synthesized compounds demonstrate that active pyrroloquinolinone derivatives strongly bind in the colchicine site of β-tubulin. In the experiment, the researchers used many compounds, for example, 1-Chlorooctadecane (cas: 3386-33-2Synthetic Route of C18H37Cl).
1-Chlorooctadecane (cas: 3386-33-2) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Synthetic Route of C18H37Cl
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics