Adel A. El-Gendy

Synthesis and Biological Activity of Functionalized Indole-2-carboxylates, Triazino- and Pyridazino-indoles

Condensation of aryl hydrazines with ethyl pyruvate gave the respective hydrazones 4–6; Fischer indolization led to substituted‐1H‐indole‐2‐carboxylic acid ethyl esters 7–9. The Mannich reaction of these compounds with formaldehyde and morpholine yielded ethyl 3‐(morpholinomethyl)‐substituted‐1H‐indole‐2‐carboxylates 10‐12. The 5,7‐dichloro‐1H‐indole‐2‐carbohydrazide 13 was cyclized with methyl orthoformate in DMF to give 6,8‐dichloro[1,2,4]triazino[4,5‐a]indol‐1(2H)‐one 14. Vilsmeier–Haack formylation of 7–9 gave ethyl 3‐formyl‐substituted‐1H‐indole‐2‐carboxylates 15–17 whose 2,2′‐((5‐chloro‐2‐(ethoxycarbonyl)‐1H‐indol‐3‐yl)methylene)bis‐(sulfanediyl) diacetic acid 18 was prepared. The reaction of 15 and 16 with substituted anilines by conventional and microwave methods gave ethyl 3‐(N‐aryliminomethyl)‐5‐halo‐1H‐indole‐2‐carboxylates 19–29. In a cyclocondensation reaction of 19–25 with thiolactic acid or thioglycolic acid substituted indolylthiazolidinones 30–33 were prepared. Reaction of hydrazine hydrate with 15–17 did not give the respective hydrazones but directly led to the cyclized products substituted‐3H‐pyridazino[4,5‐b]indol‐4(5H)‐ones 34–36, while a reaction with 2,4‐dichlorophenylhydrazine yielded the uncyclized hydrazones. The chlorination of 35 and 36 with POCl3 gave pyridazino[4,5‐b]indoles 39 and 40, respectively; reaction of the latter compounds with morpholine gave 4‐(substituted‐5H‐pyridazino[4,5‐b]indol‐4‐yl)morpholine 41 and 42. Mannich reaction of 34 with formaldehyde and N‐ethylpiperazine gave 8‐chloro‐3‐((4‐ethylpiperazin‐1‐yl)methyl)‐3H‐pyridazino[4,5‐b]indol‐4(5H)‐one 43. The microwave assistance of selected reactions has a profound effect on the reaction speed. The structures of the new compounds were confirmed by both analytical and spectral data. Some compounds were subjected to investigations concerning their antimicrobial, tranquilizing, and anticonvulsant activities.

Synthesis and antimicrobial activity of some new 2-indolinone derived oximes and spiro-isoxazolines.

The synthesis and spectral analysis of some new 1,3-dihydro-3-hydroxy-3-[2-hydroxyimino-2-(substituted phenyl)ethyl]-2H-indol-2-ones (21–32) and spiro[3H-indol-3,5/t’-(4/t’H)-isoxazol]-2(1H)-ones (33–44) are described. Sixteen of the synthesized compounds were screenedin vitro for their growth inhibitory activity against thirteen species of microorganisms,viz, S. aureus, S. epidermidis, S. faecalis, B. subtilis, B. cereus, E. aerogens, E. coli, P. aeruginosa, P. vulgaris, A. baumonia, A. faecalis, C. albicans andS. cervicae. Most of the compounds exhibited significant antimicrobial activity especially the oximes28 and29.

Synthesis of some quinoxaline derivatives containing indoline-2,3-dione or thiazolidinone residue as potential antimicrobial agents

The synthesis of some quinoxaline derivatives containing indoline-2,3-dione or thiazolidinone residue is described. The synthesized derivatives were screenedin vitro for their growth inhibitory activity against six species of bacteria, viz.Staphylococcus aureus, Streptococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Serratia marcescens andMycobacterium semegmatis. Most of the compounds exhibited antimicrobial activity especially those having indoline-2,3-dione moiety.

Synthesis of 1H-Indole-2,3-Dione-3-Thiosemicarbazone Ribonucleosides as Antibacterial Agents

A new isatin ribonucleoside (3) was synthesized in a good yield by trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed coupling reaction between the silylated nitrogenated base of 1H-Indole-2,3-dione (1) and 1,2,3,5-tetra-O-acetyl-β-D-ribfuranose (2). Thiosemicarbazides 4a–e were utilized by the prepared ribonucleoside (3) to give new series of 1H-indole-2,3-dione-3-thiosemicarbazone ribonucleosides 5a–e. All compounds tested as antibacterial agents showed slight inhibitory activity against the selected bacterial strains.

Synthesis and antihypertensive activity of certain Mannich Bases of 2-ethoxycarbonylindoles and 5H-pyridazino[4,5-b]indoles

This manuscript reports the synthesis of two series of Mannich Bases 3–12 and 21–40 obtained respectively by the reaction of either 2-ethoxycarbonylindoles 1–2 or 5H-pyridazino [4,5-b]inoles 17–20 as a substrate with formalin and the appropriate 2° amines under the suitable Mannich conditions. Fourteen of the synthesized Mannich basese were screened as antihypetensive agents in normotensive anesthetized rats. The effect of compound 4 in normotensive anesthetized dogs was also studied.

Synthesis of new 9-glycosyl-4,9-dihydropyrano [3,4-b]indole-1(3H)-ones as antibacterial agents.

A series of new 9-glycosyl-4,9-dihydropyrano[3,4-b]indole-1(3H)-ones 3 was synthesized in moderate to low yields. 4,9-Dihydropyrano[3,4-b]indole-1(3H)-ones (1) were coupled with different acetobromoglycopyranoses 2 in refluxing toluene in the presence of silver oxide to afford one coupling product of the respective N-glycosides. α-L-Arabinopyranosides 3j and 3m were the most active glycosides among the tested compounds against certain Gram positive and Gram negative bacterial strains.