Study on Quinazolinone and Thiazolidinone

 Study on Quinazolinone and Thiazolidinone Dissertation

General Papers

ARKIVOC 2006 (i) 109-118

Activity and primary virocide activity evaluation of 3-hydrazono-5-nitro-2-indolinone derivatives Nalan TerzioДџlu *a, NilgГјn KaralД± a, Aysel GГјrsoy a, Christophe Pannecouque b, Pieter Leysen n, Jan Paeshuyse b, Johan Neyts w, and Erik De Clercq b a

Istanbul College or university, Faculty of Pharmacy, Division of Pharmaceutical Chemistry, 34116, Istanbul, Poultry b Rega Institue of Medical Study, Katholieke Universiteit Leuven, B-3000 Leuven, Belgium E-mail: [email protected] com

Subjective A series of 5-nitro-3-[(5-nonsubstituted/methyl-4-thiazolidinone-2-ylidene)hydrazono]-1H-2indolinones (3a-j and 4a-h) was synthesized simply by cyclization of 5-nitro-1H-indole-2, 3-dione-3thiosemicarbazones (1a-k) with ethyl bromoacetate or ethyl 2-bromopropionate. The primary antiviral activities of the fresh hydrazonoindolinone derivatives, the recently reported 5-nitro1H-indole-2, 3-dione-3-thiosemicarbazones (1a-k) and 1-morpholino/piperidinomethyl-5-nitroindole-2, 3-dione-3-thiosemicarbazones (2a-l) were assessed against several pathogenic viruses in the Rega Institue intended for Medical Exploration, Belgium. Among the tested compounds, 1c, 2b and 3b afforded a few weak activity against the yellow-colored fever malware (YFV) in vero cellular material, whereas substances 2b, 3a, 3f, 4e and 4f inhibited the expansion of boeotian viral diarrhea virus (BVDV) in MDBK CODA cells. Keywords: 1H-2-Indolinones, 4-thiazolidinones, virocide activity


Isatin (1H-indole-2, 3-dione) is a versatile lead molecule pertaining to designing potential antiviral providers. Several creators found that isatin-ОІ-thiosemicarbazone (1H-indole-2, 3-dione-3thiosemicarbazone) and its N-Mannich facets were active against various viruses1. The first clinically approved virocide agent, N-methylisatin-ОІ-thiosemicarbazone (methisazone, I), and isatin-ОІ-thiosemicarbazone (II) are active against poxviruses2. Antiviral properties of certain thiourea and semicarbazone derivatives have been reported where the antiviral impact is caused by the presence of a great intact NHC(=S)NH grouping and NHC(=O)NH grouping3. The cyclic urea derivative (III), like a replicase inhibitor specific for the bovine virus-like diarrhea virus (BVDV)4 continues to be recently recognized. On the other hand, several original 4-thiazolidones are

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General Papers

ARKIVOC 2006 (i) 109-118

undergoing different stages of trials as potential antimicrobial, antiviral, anticancer and thrombolytic prescription drugs. It has been reported that members of a group of 2, 3-diaryl-1, 3-thiazolidin-4ones were highly effective in inhibiting the cytopathic a result of HIV-1 in human T-lymphocyte cells5. The 2-thioxo-4-thiazolidone type, epalrestat (IV) is a remarkably active aldose reductase inhibitor (Figure 1). S In NH O N R1

I 2

R1= CH3, R2= L R1=R2= H

R2 N R


N N N And O N H





Figure you In view of these types of observations, we report right here the synthesis of the new 5-nitro-3-[(5nonsubstituted/ methyl-4-thiazolidinone-2-ylidene)hydrazono]-1H-2-indolinones (3 and 4) and evaluation of in vitro antiviral process of these new compounds plus some of the recently reported 5-nitro-1H-indole-2, 3-dione-3-thiosemicarbazones (1) and 1-morpholino/ piperidinomethyl-5-nitro-indole-2, 3-dione-3-thiosemicarbazones (2).

Effects and Discussion

Treatment of ethyl bromoacetate or ethyl 2-bromopropionate with 5-nitro-1H-indole-2, 3-dione3-thiosemicarbazone 1a-k in anhydrous ethanolic method furnished the corresponding 5-nitro-3[(5-nonsubstituted/methyl-4-thiazolidinone-2-ylidene)hydrazono]-1H-2-indolinones (3a-j and 4a-h) (Scheme 1). The set ups of 3 and 4 had been confirmed simply by analytical and spectral info (IR, 1H NMR, 13C NMR and EIMS) (Table 1). Inside the IR spectra of 3 and 4, the C=S groups disappeared, a new C=O strap (1756-1734 cm-1) indicative of the thiazolidinone structure appeared besides the lactam C=O stretching (1705-1689 cm-1)6. 1H-NMR spectra of three and 5 did not...

Recommendations: 464. (c) Balzarini, L.; Naesens, D.; Slachmuylders, T.; Niphuis, H.; Rosenberg, My spouse and i.; Holy, A.; Schellekens, L.; De Clercq, E. ASSISTS 1991, five, 21. (d) Neyts, J.; Meerbach, A.; McKenna, P.; De Clercq, E. Virocide Res. 1996, 30, a hundred and twenty-five.