Selectivity of N‐aroyl‐N′‐arylthioureas towards 2‐(1,3‐dioxo‐1H‐inden‐2(3H)‐ylidene)malononitrile. New synthesis of (Z)‐N‐((E)‐4‐amino‐1‐aryl‐5‐cyano‐6‐oxo‐1H‐indeno[1,2‐d][1,3]‐ thiazepin‐2(6H)‐ylidene)‐4‐arylamides of antitumor and antioxidant activities

Abstract

in Wiley InterScience (www.interscience.wiley.com). The reaction between N-aroyl-N 0 -arylthioureas with 2-(1,3-dioxoindan-2-ylidene)malononitrile furnished indeno[1,2-d][1,3]thiazepines in 70-85% yields. The mechanism of the products' formation is discussed. Some of the products showed effective antitumor and antioxidant activities. The results revealed that compound indenothiazepine derivative showed a high inhibition of the cell growth of Hep-G2 cells is compared with the growth of untreated control cells, as concluded from their low IC 50 value 21.73 lM. On the other hand, two indenothiazepine derivatives have an effective antioxidant activity with SC 50 values of 62.5 mM and 87.4 mM, respectively. J. Heterocyclic Chem., 47, 503 (2010).Scheme 1. Reactions of aroyl thioureas 1a-e with 2; synthesis of (Z)-N-((E)-4-amino-1-aryl-5-cyano-6-oxo-1H-indeno[1,2-d][1,3]thiazepin-2(6H)ylidene)-4-arylamides 3a-e. 3a: 75%; 3b: 80%; 3c: 85%; 3d: 82%; 3e: 70%.Scheme 2. Suggested mechanism of the reaction of 1a-e with 2. 504Vol 47

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

“…[49] A small, focused library of substituted 2-aminobenzothiazoles (Scheme 10) was prepared by solid-phase synthesis, involving the cyclization of 1-acyl-3-phenyl thioureas. Hydrazine monohydrate was used as a useful deprotecting agent.…”

Computer prediction and synthesis of new azoles based on N-benzoyl-N'-(9,10-dioxo-9,10-dihydroanthracen-1-yl)thioureas

“…On the other hand, N-aroylthioureas have a strong synthetic potential. They are important reagents for the synthesis of several heterocycles, such as imidazolidinyl-2thiones [1,2], 2-aroyliminothiazolines [3][4][5], 1,2,4triazoles [6], 1,3-thiazines [7] and indeno [1,2d] [1,3]thiazepines [8]. 2-Iminothiazolines are characterized by a wide range of biological properties [9][10][11][12].…”