Project hareesh
- 1. k.Tharangini k.Priyanka v.Hareeshkumar (16Q01R0091) (16Q01R0059) (16Q01R0022) S.Varunkumar J.Manjula M.Sunanda (16Q01R0093) (16Q01R0040) (16Q01R0084) M.Chandrasekhar M.Madhu sudhana (16Q01R0014) (16Q01R0037) Under the guidance of DR.P.R.Logesh kumar,M.pharm,Ph.D.., Associate Professor Department of pharmaceutical chemistry. SRI KRISHNA CHAITHANYA COLLEGE OF PHARMACY,MADANAPALLE. Synthesis Experiments and pharmacological screening of some novel Cinnoline derivatives Presented by
- 2. ļ¶Cinnoline is also known as 1,2-diazanaphthalene or benzo-1,2-diazene ļ¶Cinnoline itself is toxic.The starting compound of cinnoline is Anilineand Sodium nitrite. ļ¶It is a pale yellow solid of geranium like odour. NUCLEUS INTRODUCTION CINNOLINE other name:Benzopyridazine Molecular formula C8H6N2 Molecular weight 130gm Melting point 38oC Boiling point 0.351140mmHg Solubility Ethanol,Methanol,DMSO,DM F
- 3. ļ¶Aniline and its ring-substituted derivatives react with nitrousacid to form diazonium salts ļ¶Its main use in the manufacture of precursors to polyurethane and other industrial chemicals. ļ¶IN this reaction primary aromatic amine reacts with sodium nitrite and with 2mloes of HCL as major product and water and sodium chloride. INTRODUCTION TO STARTING MATERIAL ANILINE Other names:Phenylamine,Aminobenzene,Benzamine Molecular formula C6H7N Molecular weight 93.129gm Melting point -6.3oC Boiling point 184.13oC
- 4. ļ¶S . Hurmath Unnisa* Et.al , Synthesis and screening of pyrazole based cinnoline derivatives for its anti tubercular and anti fungal activity was synthesized . ļ¶Sony . S* Et.al , A concise review on cinnoline and its biological activities . LITERATURE REVIEW
- 5. ļ¶Literature servey reveals that,the derivatives of Cinnoline have high potential biological activity,processing a wide range of anti fungal activity.Biological derivatives Cinnoline like anti-inflammatory,anti- bacterial,anti-fungal. ļ¶Collected literature from various journals Synthesized of Cinnoline derivatives 1) Melting point 2) Boiling point 3) Solubility ļ¶Characterised the synthesis compounds of spectral methods. ļ¶Evaluated the biological activity of newly synthesized compounds PLAN OF WORK
- 6. STEP-1: 1-chloro-2-phenyl diazene is prepare by dissolving sodium nitrite(0.1 mole) in 26ml of water and added drop wise to a solution of amine(10ml in 1N HCL) at 0oc under stirring for about 30mins and reflux for 1hr. Then orange coloured precipitate is collect by filtration and dried. Ethanol,1Hr STEP-2: To a solution of compound(0.2 mole) in ethanol,pentane 2,4dione(0.2 mole) is added. The mixture is refluxed for 5 hours. The solvent is evaporated and the solid obtained is recrystalized from petroleum ether. Ethanol,pentane-2,4-dione EXPERIMENTAL WORK
- 7. STEP-3: Compound 2 (0.1 mole) in ethanol (10ml),20ml of poly phosphoric acid is added. The mixture is maintained under reflux for 6 hours. After cooling,the mixture is poured on ice and the solid formed is collected by filtration,washed with cold water and recrystalized from ethanol. Polyphosphoric acid,6H STEP-4: Compound 3(0.1 mole) in 30ml of ethanol and 30ml of formaldehyde. The mixture is maintained under reflux for 6 hours. The solvent is evaporated and the solid obtained is recrystalized from petroleum ether. Ethanol,formaldehyde,6H
- 8. MATERIALS AND INSTRUMENTS ļ INSTRUMENTS ļ± VEEGO Digital melting point apparatus. ļ± Perkin elmer spectrum version 10.03.07.IR spectrometer ļ± JEOL GC mate mass spectrometer ļ± UV spectroscopy ļ± Hot air oven,Thermometer ļ± Single pan electronic balance ļ± Heating mantle,Incubator ļ± Ultra sonicator ļ CHEMICALS ļ± Aniline ļ± Sodium nitrite ļ± Ethanol ļ± Pentane-2,4-dione ļ± Poly phosphoric acid ļ± Formaldehyde ļ± Sodium nitropruside ļ± Phosphate buffer ļ± Griess reagent
- 9. Melting point and appearance PHYSICAL CHARACTERISATION S.NO Compoun d code Melting point Appearan ce % of yield 1 compoun d1 80 0c Pure white 93% 2 compoun d2 76 0c White 86% 3 compoun d3 77 0c White 84% 4 compoun d4 82 0c white 82% 5 A1 140 0c Colourles s solid powder 90% 6 A2 138 0c White crystals 88% 7 A3 153 0c Colourles s or white 91%
- 11. The purity of all synthesized compounds was monitored on TLC THIN LAYER CHROMATOGRAPHY S.NO Compound code Rf value 1 compound1 0.51 2 compound2 0.14 3 compound3 0.83 4 compound4 0.82 5 A1 0.82 6 A2 0.68 7 A3 0.84
- 12. The molecular formula and molecular weight of all the synthesized compounds are given MOLECULAR FORMULA AND MOLECULAR WEIGHT S.NO Compound code Molecular formula Molecular weight(gm) 1 compound1 C6H5ClN2 146.5gm/mol e 2 compound2 C11H12N2O 2 204gm/mole 3 compound3 C11H12N2O 188gm/mole 4 compound4 C13H17N2O 217gm/mole 5 A1 C7H6O2 122.12gm/m ole 6 A2 C7H6O3 138.12gm/m ole 7 A3 C6H8O7 192.12gm/m ole
- 13. INTRODUCTION NMR spectroscopy is powerful analytical technique used to charaterised organic molecules by identified carbon-hydrogen frame works with in molecules To common types of NMR spectroscopy are used to charaterised organic structure 1 H NMR is used to determine the type and number of H atoms in a molecule 13C NMR is used to determine the type of carbon atoms in the molecule Source of energy in NMR is radio waves which have long wavelength and thus low energy and frequency When low energy radio waves interact with a molecule, they can change the nuclear spins of some elements including 1H and13C. PRINCIPLE OF NMR SPECTROSCOPY Nuclei of all elements carry a charge. When the spins of the protons and neutrons comprising these nuclei are not paired, the overall spin of the charged nucleus generates a magnetic dipole along the spin axis, and the intrinsic magnitude of this dipole is a fundamental nuclear property called the nuclear magnetic moment, Āµ. The symmetry of the charge distribution in the nucleus is a function of its internal structure and if this is spherical (ie analogous to the symmetry of a 1s hydrogen orbital), it is said to have a corresponding spin angular momentum number of I=1/2, of which examples are 1H, 13C, 15N, 19F, 31P etc. Nuclei which have a non-spherical charge STRUCTURAL CONFIRMATION
- 14. USES OF NMR SPECTROSCOPY NMR used in biology to study the biofluids,cell,perfused organs and biomacromolecules such as nucleic acid (DNA , RNA) carbohydrates , proteins and peptides . And also labeling studies in laboratory. NMR is used in physics and chemistry to study high pressure diffusion ,liquid crystals ,liquid crystals solution ,membrane ,rigid solids. NMR is used in food science. APPLICATIONS OF NMR NMR spectroscopy is a non destructive analytical technique that is used to probe the nature and characteristic of molecular structure .A simple NMR experiment produces information in the form of a spectrum ,which is able to provide details about; The type of atoms present in the sample The relative amount of atoms present in a sample The specific environments of atoms with in a molecule The purity and composition of a sample Structure information about a molecule ,including constructional and conformational isomerisation.
- 15. INTRODUCTION Chromatographic theory describes the physicochemical relationships governing separations. Usually, semiempirical models of the chromatographic process that have a relatively simple thermodynamic background and give a bulk picture of the physical or chemical phenomena are involved. Macroscopic models of the chromatographic process cannot mirror the respective separation mechanisms in any other way. Exceptions to this rule, if any exist, are rather negligible. It is important to keep in mind two facts. First, one always has to be aware of the complexity of chromatographic processes, and consequently of limitations of the existing semiempirical models. BASIC PRINCIPLE chromatography works on the principle that different compounds will have different solubilities and adsorption to the two phases between which they are to be partitioned. Thin Layer Chromatography (TLC) is a solid-liquid technique in which the two phases are a solid (stationary phase) and a liquid (moving phase THIN LAYER CHROMATOGRAPHY
- 16. PROCEDURE With a pencil, a thin mark is made at the bottom of the plate to apply the sample spots. Then, samples solutions are applied on the spots marked on the line in equal distances. The mobile phase is poured into the TLC chamber to a leveled few centimeters above the chamber bottom. A moistened filter paper in the mobile phase is placed on the inner wall of the chamber to maintain equal humidity (and also thereby avoids edge effect this way). Now, the plate prepared with sample spotting is placed in the TLC chamber so that the side of the plate with the sample line is facing the mobile phase. Then the chamber is closed with a lid. The plate is then immersed, such that the sample spots are well above the level of mobile phase (but not immersed in the solvent ā as shown in the picture) for development. Applications To check the purity of the given samples. Identification of compounds like acids, alcohols, proteins, alkaloids, amines, antibiotics, and more.
- 23. In-vitro antioxidantactivity : All the compounds were subjected to in-vitro antioxidant RESULTS AND DISCUSSION
- 27. Pharmacology pharmacology is a separate discipline in the health sciences. Pharmacology is the study of how a drug affects a biological system and how the body responds to the drug. The discipline encompasses the sources, chemical properties, biological effects and therapeutic uses of drugs. Pharmacology has two major branches: Pharmacokinetics, which refers to the absorption, distribution, metabolism, and excretion of drugs. Pharmacodynamics, which refers to the molecular, biochemical, and physiological effects of drugs, including drug mechanism of action. PHARMACOLOGY
- 28. Chemotherapy of fungal diseases CHEMOTHERAP Y OF FUNGAL DISEASES
- 51. THANK YOU
- 52. Presented By: SEMINAR ON CHEMOTHERAPY OF FUNGAL M.Madhu sudhana(16Q01R0037) 4Th Year B.Pharmacy Sri Krishna Chaithanya College Of Pharmacy Madanapalle