Discovery of Tröger's base analogues as selective inhibitors against human breast cancer cell line: Design, synthesis and cytotoxic evaluation

Diastereoselective Self‐Assembly of a Neutral Dinuclear Double‐Stranded Zinc(II) Helicate via Narcissistic Self‐Sorting

“…Then as olution of zinc(II) acetatedihydrate (39.1 mg, 0.18 mmol, 1equiv) in ethanol (1 mL) was added dropwise, and the resulting mixture was refluxed for 2h ours and stirred at ambient temperature for another 12 hours. The resulting solid was filtered, washed with ethanol (1 mL), and dried in vacuo to yield the desired product as ay ellow solid (34 mg, 34 4.20 (s,2H,4.42 (d,2H,H exo ,2 J H-exo,H-endo = À16.2 Hz), 6.69 (ddd,2H,4 J H-23,H-25 = 1.2 Hz), 6.78 (d, 2H,H -25, 3 J H-25,H-24 = 7.7 Hz), 6.85 (s, 2H, H-1, H-7), 7.08 (s,2H,7.39 (ddd,2H,7.49 (dd,2H,3 C6 6.13, H4 .69, N9 .90, found:C66.07, H4 .95, N 9.80.…”

“…The unique shape and the N-centered chirality of Trçger's base has been fascinating chemists for more than ac entury now, [1] and thus, this scaffoldh as found numerous applicationsi n many different areas such as medicinal chemistry, [2] optoelectronics, [3] as ligandsf or transition metal catalysts, [4] as microporous polymers, [5] as chiral auxiliaries, [6] or in supramolecular chemistry. [7] Based on Wärnmark's versatile protocol for the preparation of functionalized Trçger's base derivativess tarting from simple functionalized anilines, [8] we have also made some contributions to this field by synthesizingn ew derivatives and achieving their chiral resolution via HPLC on chiral stationary phases, [9] and the Trçger'sb ase scaffold turned out to be at ruly privileged V-shaped structuralm otif for the formation of stereochemically well-definedm etallosupramolecular aggregates in our hands.…”

Combinatorial Chemistry Online Volume 17, Issue 1, January 2015

“…The structurally diverse frameworks were evaluated for their cytotoxic activities against a panel of three human cancer lines: A549 (lung adenocarcinoma), MDAMB-231 (breast) and SK-N-SH (neuroblastoma). From the activity profile obtained, a redesign of the analogues led to the construction of more potent molecular entities, and the development of compounds with MDAMB-231 cell line specific cytotoxicity [15].…”

Synthetic strategies and diversification of dibenzo[1,5]diazocines

“…These derivatives bear a close resemblance to Tröger's base which is of particular interest as a building block for supramolecular chemistry. 2 Dibenzo[1,5]diazocines and analogues attract attention in diverse research endeavours because selected derivatives have shown impressive activity in a wide range of biological assays such as DNA intercalation, 3 inhibitors against cancer cells, 4,5 pregnancy inhibitors, 6 molecular receptors, 7 histone deacetylase (HDAC) inhibitors, 8 enzyme inhibition 9 and as hosts in molecular recognition. 10 The alkaloid-based diazocine can also be extracted naturally from the marine mudflat as an oxysporizoline and displays modest anti-bacterial and radical scavenging activities.…”