Synthesis and photodynamic properties of pyrazole-indole hybrids in the human skin melanoma cell line G361

Convenient Synthesis of Pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazoles via Intramolecular Nitrile Oxide Cycloaddition

“…We previously investigated the metal-free intramolecular alkyne-azide cycloaddition reaction for the formation of the pyrazolo [4,3-f ] [1,2,3]triazolo [5,1-c] [1,4]oxazepine ring system [26] as well as the synthesis of 2,6-dihydropyrano [2,3-c]pyrazole derivatives by employing the ring-closing metathesis (RCM) reaction [27]. In continuation of our interest in the synthesis and investigation of novel pyrazole-containing polyheterocyclic systems [28][29][30][31][32][33], we report herein the synthesis and structural elucidation of new 3a,4dihydro-3H,7H-and 4H,7H-pyrazolo [4 ,3 :5,6]pyrano [4,3-c] [1,2]oxazole derivatives from appropriate 3-(prop-2-en-1-yloxy)-or 3-(prop-2-yn-1-yloxy)-1H-pyrazole-4-carbaldehyde oximes via the intramolecular nitrile oxide cycloaddition reaction.…”

Recent Developments in the Synthesis of Indole‐Pyrazole Hybrids

“…Using the strategies described in Scheme 69, ethyne, ethene and 1,3‐butadiene‐linked indole‐C5 pyrazole hybrids ( 383 , 385 & 388 ) were synthesized and studied their photodynamic properties in human skin melanoma cell line (G361) by Varvuolyte and co‐workers [122] . The starting material 3‐(hexyloxy)‐1‐phenyl‐1 H ‐pyrazole‐4‐carbaldehyde ( 380 ) was readily formed from 3‐hydroxy‐1‐phenyl‐1 H ‐pyrazole via sequential O ‐alkylation (Williamson ether synthesis) and Vilsmeier‐Haack formylation reactions.…”

“…Using the strategies described in Scheme 69, ethyne, ethene and 1,3-butadiene-linked indole-C5 pyrazole hybrids (383, 385 & 388) were synthesized and studied their photo- dynamic properties in human skin melanoma cell line (G361) by Varvuolyte and co-workers. [122] The starting material In 2015, Kamal et al reported the synthesis and anticancer evaluation of a series of (Z)-(arylamino)-pyrazolyl/isoxazolyl-2propenones. [123] Indole-bearing pyrazole derivatives ( 396 a Kandeel et al synthesized a methine-linked indole-C5 pyrazole hybrid (399) in two steps as shown in Scheme 71.…”

Pyrazole-based lamellarin O analogues: synthesis, biological evaluation and structure–activity relationships

“…[29][30][31] Replacement of the central pyrrole to pyrazole is expected to change e.g., the energy of the highest occupied molecular orbital (HOMO) which is associated with increased metabolic stability. 32 In continuation of our previous works devoted to synthesis and investigation of pyrazole derivatives, [33][34][35][36][37][38][39][40][41] in this study we ought to synthesize and investigate various functionalized pyrazole derivatives of lamellarin O. The goal was based on the scaffold hopping of the pyrrole ring in natural lamellarin O to its pyrazole counterpart.…”