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Synthesis, Spectroscopy, Computational and Anticancer ienc Sc es al J c o i u Shalof et al., Chem Sci J 2018, 9:3 m r e n a h DOI: 10.4172/2150-3494.1000196 l C Chemical Sciences Journal ISSN: 2150-3494 Research Article Open Access Synthesis, Spectroscopy, Computational and Anticancer Evaluation of Some Novel Isatin Derivatives Rabab T Shalof*, Eman H Tawfik and Fadda AA Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt *Corresponding author: Rabab T Shalof, Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, 35561, Egypt, Tel: 002-050-2242388; E-mail: [email protected] Received date: September 22, 2018; Accepted date: October 15, 2018; Published date: October 30, 2018 Copyright: © 2018 Shalof RT, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Abstract A series of Isatin derivatives was synthesized using potassium 2-cyano-3-oxo-3-(2-(2-oxoindolin-3- ylidene)hydrazinyl)-1-(phenylamino)prop-1-ene-1-thiolate (2) as starting material. Compound (2) reacts with various reagents under different conditions to give the corresponding thiazol, thiophen and pyridine derivatives, which were characterized by elemental analysis, spectroscopy (1H-NMR, IR and Mass spectra). The anticancer activities of the newly synthesized compounds were studied against colon carcinoma cells by using the Minimum Inhibition Concentration (MIC) method. Compounds belonging to 8, 12 and 13 series produced a high anti-cancer reactivity. Keywords: Isatin; Heterocyclic; Thiazol; Thiophen; Pyridine; the synthesis of some new heterocycles incorporating an indole moiety Antimicrobial activity starting from cyanoacetohydrazide and Isatin, we found that 2-cyano- N'-(2-oxoindolin-3-ylidene) acetohydrazide (1) [20] is a highly active Introduction against tumor cells and useful building for the synthesis of a variety of phenylthiazolidin, phenylthiazol and thiophene derivatives Isatin or 1H-indole-2,3-dione is an indole derivative. The compound incorporating satin moiety of potential biological activity. was first obtained [1,2] as a product from the oxidation of indigo dye by nitric acid and chromic acid. Isatin forms a blue dye if it is mixed Materials and Methods with sulfuric acid and crude benzene. The formation of the blue indophenin was long believed to be a reaction with benzene. Victor Meyer was able to isolate the substance responsible for this reaction Instruments from benzene. This new heterocyclic compound was thiophene [3]. All melting points (m.p.) are recorded in Gallenkamp electric m.p. Isatin is exerting a broad spectrum of biological activity like antipyretic apparatus and are uncorrected. The IR spectra νcm-1 (KBr) were activity, analgesic effect anticonvulsant activity; few compounds were recorded in Perkin Elmer Infrared Spectrophotometer Model 157, also reported as psychotropic agents and Monoamine Oxidase (MAO) Grating. The 1H-NMR spectra were run on Varian Spectrophotometer inhibitors [3]. at 300 and 75 MHz, respectively, using Tetramethylsilane (TMS) as an Isatins are an important group of heterocyclic compounds which are internal reference and DMSO-d6 as solvent. The mass spectra (EI) were biologically active and of significant importance in medicinal recorded on 70 eV with Kratos MS equipment and/or a Varian MAT chemistry. A literature survey identified several Isatin derivatives in the 311 A Spectrometer at Micro analytical Unit, Faculty of Science, Cairo development phase as potential new drugs. Isatin (1H-indole-2,3- University and Al-Azhar University, Cairo, Egypt. Elemental analyses Dione) and its derivatives exhibit various biological activities such as (C, H and N) were carried out at the micro analytical center of Cairo anticancer [4], anticonvulsant [5], anti-inflammatory [6], University, Giza, Egypt, the results were found to in good agreement (± antimicrobial, antiviral [7] and anti neo-plastic activities [8]. These 0.3%) with the calculated values. Antimicrobial screening for the compounds are versatile building blocks for the synthesis of a large selected new compounds was carried out in the regional center for variety of heterocyclic compounds such as indoles, isotopic anhydride, mycology and biochemistry, Al-Azhar University, Cairo, Egypt. quinolines, spirooxin-doles, and etc. The unique structural array of these compounds has made them attractive synthetic targets in Chemistry chemistry. Isatins are capable of crossing the blood-brain-barrier [9]. Potassium-2-cyano-3-oxo-3-(2-(2-oxoindolin-3- Isatin, a heterocyclic compound was identified in animals as a major ylidene)hydrazinyl)-1(phenylamino)prop 1-ene-1-thiolate (2): The component of the endogenous MAO inhibitors. The various reaction of 2-cyano-N'-(2-oxoindolin-3-ylidene) acetohydrazide (1) substituents at 3rd position of the Isatin which were reported various with phenyl isothiocyanate in the presence of potassium hydroxide in substituted phenyl ring moieties, heterocyclic rings and aliphatic Dimethylformamide (DMF) to give a potassium 2-cyano-3-Oxo-3-(2- system. Isatin (1H-Indole-2,3-dione) is one of the most promising new (2-oxoindolin-3-ylidene)hydrazinyl)-1-(phenylamino)prop-1-ene-1- class of heterocyclic molecules having many interesting activity profiles thiolate (2) was prepared as previously described [21]. and well-tolerated in human subjects. As a continuation of our efforts 2-cyano-3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)-N- [10-19] to identify new condition that may be of value in designing phenylpropanethioamide (3): To a stirred solution of potassium new, potent, selective, less toxic antimicrobial agents, we report here hydroxide (0.01 mol) in N,N-DMF (20 ml) was added compound (1) Chem Sci J, an open access journal Volume 9 • Issue 3 • 1000196 ISSN: 2150-3494 Citation: Shalof RT, Tawfik EH, Fadda AA (2018) Synthesis, Spectroscopy, Computational and Anticancer Evaluation of Some Novel Isatin Derivatives. Chem Sci J 9: 196. doi:10.4172/2150-3494.1000196 Page 2 of 6 (0.01 mol). After the mixture was stirred for 30 min, phenyl 2-cyano-3-((2-oxo-2-phenylethyl)thio)-N'-(2-oxoindolin-3- isothiocyanate (0.01 mol) was added to the resulting mixture. Stirring ylidene)-3-(phenylamino)- acrylohydrazide (4e): Dark brown crystals; -1 was continued at room temperature for 12 hrs. The reaction mixture 211-213°C; (85%); IR (KBr) νmax cm : 3450 (NH), 3327 (NH), 3193 1 was acidified with cold dilute HCl. The solid product that separated (NH), 2218 (CN) 1729, 1693 (2C=O); H-NMR (DMSO-d6, δ, ppm): 1 was filtered, washed with water and recrystallized from ethanol to give 4.03 (s, 2H, CH2), 6.96-7.46 (m, 9H, ArH), 10.03 (S, H, NH-amid), (3) [10]. 10.34 (s, 1H, NH), 12.133 (s, 1H, NH-hydrazid). MS m/z (%): 481 (M+ +1, 100), 482.12 (28.1%), 484.12 (4.5%), 483.13 (2.7%). Anal. for: 3-(argiothio)-2-cyano-N'-(2-oxoindolin-3-ylidene)-3- C H N O S (M. wt. 481): Calc.: C, 64.85; H, 3.98; N, 14.54. Found: (phenylamino)acrylohydrazide (4a-e): Equal molar amounts of (2) 26 19 5 3 C, 64.87; H, 4.00; N, 14.56%. (0.01 mol) in DMF (20 ml) were stirring, then added appropriate 2- chloroacetylchloride, ethyl 2-bromoacetate, 2-chloroacetone, 2- 2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)-N'-(2- chloroacetonitrile and phenyl bromide (0.01 mol) was added portion oxoindolin-3-ylidene)-acetohydrazide (5): Equal molar amounts of (2) wisely over a period of 30 min. After the addition was complete, the (0.01 mol) in DMF (20 ml) were stirring, then added appropriate 2- reaction mixture was stirred for 24 hrs the intermediates (4(a-e)) was chloroacetylchloride (0.01 mol) and ethyl 2-bromoacetate (0.01 mol) formed. Then poured onto crushed ice containing hydrochloric acid, the reaction mixture was stirred for 24 hrs the intermediates was the solid product was filtered off, washed with ethanol, dried and formed (4(a,b)). After 24 hrs the reaction mixture was heated under crystallized from an ethanol\DMF mixture to give the compound (4(a- reflux for 5 hrs and then poured onto crushed ice containing e)). hydrochloric acid. The formed solid product was filtered off, washed with ethanol, dried and crystallized from an ethanol\DMF mixture to 2-((2-cyano-3-oxo-3-(2-(2-oxoindolin-3- give the compound (5); dark brown crystals; 250-252°C; (85%); IR ylidene)hydrazinyl)-1(phenylamino)-prop-1-en-1- (KBr) ν cm-1: 3327 (NH), 3193 (NH), 2218 (CN) 1729, 1693 yl)thio)acetylchloride (4a): Brown powder; 180-182°C; (85%); IR (KBr) max (2C=O); 1H-NMR (DMSO-d , δ, ppm): 3.22 (s, 2H, CH ), 6.96-7.46 ν cm-1: 3566 (NH), 3447 (NH), 3061 (NH), 2198 (CN), 1700, 1669 6 2 max (m, 9H, ArH), 10.03 (S, 1H, NH-amid), 11.133 (s, 1H, NH-hydrazid). and 1621 (3C=O); 1H-NMR (DMSO-d , δ, ppm): 4.45 (s, 2H, CH ), 6 2 MS m/z (%): 401.09 (M+ +1, 100), 404.08 (21.6%), 405.07 (4.5%), 6.96-7.46 (m, 9H, ArH), 10.03 (s, 1H, NH-amid), 10.44 (s, 1H, NH), 405.08 (2.2%). Anal. for: C H N O S (M. wt. 403): Calc.: C, 59.55; H, 12.133 (s, 1H, NH-hydrazid). MS m/z (%): 439 (M+ +1, 100), 440.10 20 13 5 3 3.25; N, 17.36%. Found: C, 59.57; H, 3.27; N, 17.38%. (58.0%), 436.05 (51.6%), 403.05 (26.9%). 2-(4-aryl-3-phenylthiazol-2(3H)-ylidene)-2-cyano-N'-(2- Anal. for: C H ClN O S (M. wt. 439): Calc.: C, 54.61; H, 3.21; N, 20 14 5 3 oxoindolin-3-ylidene)- acetohydrazide (6,7): A stirring of 2 (0.01 mol) 15.92.
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