Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Abstract

Two series of naphtho[1,8-ef][1,4]diazepines and pyrrolo[1,2-a]perimidines were prepared starting from 1,8-diaminonaphthalene and hydrazonoyl chlorides. The structures of the products were determined on the basis of their spectral data and elemental analyses. The mechanism of formation of such products was also discussed. The prepared compounds were screened for their antitumor activity against three cell lines, namely, MCF-7, TK-10 and UACC-62, and some derivatives showed promising activity.

Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

“…These derivatives have shown a remarkably broad spectrum of pharmacological and physiological activities and they are used as anticoagulant (Abdelhafez et al, 2010;Au and Rettie, 2008;Ganguly et al, 2013;Guo et al, 2013;Palareti and Legnani, 1996;Pelz et al, 2005;Simon and Shaughnessy, 2004;Van Walraven et al, 2002), antibacterial (Brahmbhatt et al, 2013;Cespedes et al, 2006;El-Dean et al, 2013;Kidwai et al, 2014;Kumari et al, 2013;Musthaf et al, 2013;Pansuriya and Patel, 2007;Prasad et al, 2014), antifungal (Chohan et al, 2006;Rehman et al, 2005), antiviral (Kirkiacharian et al, 2008;Zavrsnik et al, 2011), antitumor (Arya et al, 2014;Bi et al, 2013;Dorababu et al, 2013;Farghaly et al, 2014;Kawaii et al, 2001;Kumar et al, 2013;Pingaew et al, 2014;Salinas-Jazmin et al, 2010;Loa et al, 2009), anticonvulsant (Jaweed Mukarram et al, 2005), antiprotozoal (Tasdmir et al, 2006), insecticidal , fungicide (Oliva et al, 2003), antimycobacterial (Abou-Melha and Faruk, 2008;Kotharkar and Shinde, 2006;Mostafa, 2008;Sukdolak et al, 2005;Zavrsnik et al, 2008), antimutagenic …”

Fe3O4@NCs/BF0.2: A magnetic bio‐based nanocatalyst for the synthesis of 2,3‐dihydro‐1H‐perimidines

“…Perimidines constitute an important class of natural and non‐natural products. They have attracted great attention in synthetic organic chemistry for several reasons, including biological activities, pharmacological applications such as anti‐inflammatory, antibacterial, antimicrobial, antifungal, antitumor, antihypertensive, and antivirucidal agents …”

A Highly Efficient Synthesis of Pyrrolo[1,2‐a]pyrimidine Derivatives Containing 1,3‐Indandione Skeleton

“…In 2012 Rad‐Moghadam and Azimi were reported synthesis of oxindolylpyrrolo[2,3‐ d ]pyrimidines via a three‐component sequential tandem reaction of acetophenone, isatin and 6‐aminouracil by use of catalytic amount of piperidine and p ‐toluenesulfonic acid, in 2013 these type of products were synthesized with domino coupling of 6‐aminouracil, aldehydes, and nitromethane in the presence of CuFe 2 O 4 magnetic nanoparticles as catalyst . In 2014 9‐(3‐arylhydrazono)pyrrolo[1,2‐ a ]pyrimidines as antitumor agents were obtained from the reaction of HKAs containing pyrimidine ring and hydrazonoyl chlorides under basic condition in dioxane at reflux, in 2017 synthesis of pyrrolopyrimidines was reported from the reaction of 2‐nitroethene‐1,1‐diamines and α ‐bromoacetophenones in the presence of K 2 CO 3 in DMF at 120 °C 7 . Most of these methods have disadvantages such as high temperatures, metal catalysts, acidic and basic media, difficult process of catalyst preparation, harsh conditions, and etc.…”