Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Abstract

A (pyridazinyl)acetate derivative was reacted with thiosemicarbazide and hydrazine hydrate to yield spiropyridazinone and acetohydrazide derivatives, respectively. The acetohydrazide derivative was used as a starting material for synthesizing some new heterocyclic compounds such as oxoindolinylidene, dimethylpyrazolyl, methylpyrazolyl, oxopyrazolyl, cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives. The behavior of the cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives towards nitrogen and carbon nucleophiles was investigated. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, 1 H-NMR 13 C-NMR and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

Review Article; Anticancer Activities of Some Fused Heterocyclic Moieties Containing Nitrogen and/or Sulfur Heteroatoms

“…The substituents at position 2 of the pyridazinone ring do not fall into a clear pattern; alterations at this position can have major effects on the activity of the resulting compounds. Hydrazides are very useful starting materials for the construction of several heterocyclic compounds such as 1,3,4-oxadiazoles, 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4triazoles,1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines, pyrroles and pyrazoles (Shaker & Marzouk, 2016).…”

Recent applications of isatin in the synthesis of organic compounds

“…37 The newly prepared compound was tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. It was also tested as an antioxidant.…”

Synthesis, reactions, and antimicrobial activity of 2‐cyano‐N′‐(4‐(2‐oxo‐2‐phenylethoxy)benzylidene)acetohydrazide derivatives

“…Derivatives of cyanoacetic acid hydrazide are considered important intermediates and starting materials in the synthesis of many remarkable heterocyclic ring systems as they are highly reactive and polyfunctional compounds owing to having both nucleophilic and electrophilic. Additionally, they have received an excellent attention as pharmaceutical drugs [ 1,2 ] and as antibacterial agents. [ 3 ] Also, they are applicable within the industrial field in the production of dyes [ 4,5 ] and herbicides.…”