Manipal Entrance Test For MPharm and PharmD - Syllabus Of Pharmaceutical Chemistry

General principles: a brief review of classification & sources of organic compounds, sp3, sp2, sp hybridization, sigma & pi- bonds, bond lengths, bond angles & bond energies along with their significance in reactions should be carried out. An overview of bond polarization, hydrogen bonds, inductive effects, resonance, and hyperconjugation be taken. Concept of homolytic & heterolytic bond fission, acidity & basicity with different theories should be covered briefly. Ease of formation & order of stabilities of electron deficient & electron rich species along with the reasons for the same should be covered. Relationships between energy content, stability, reactivity & their importance in chemical reactions should be covered. Calculations for determining empirical & molecular formula should be covered.

Different classes of compounds: The following classes of compounds should be taught in detail with respect to their IUPAC / systematic nomenclature, industrial [wherever applicable] & laboratory methods of preparations, physical properties & chemical reactions with emphasis on reaction mechanisms [arrow based] & stereochemistry [wherever applicable], Alkanes [including cyclic compounds], Alkenes [including cyclic compounds], Alkynes [only open-chain compounds], Aliphatic hydroxyl compounds, Alkyl halides, Aldehydes & Ketones, Carboxylic acids, All functional derivatives of carboxylic acids.

Aromaticity & chemistry of aromatic compounds: Concept of aromaticity, Huckel's rule & its use in determining the aromatic/non-aromatic character of a compound. A brief coverage of structure of benzene. Detailed coverage of electrophilic & nucleophilic aromatic substitution reactions. Reactivity & orientation in these reactions. Reactivity & orientation in mono & disubstituted benzenes. Benzyne mechanism.

Different aromatic classes of compounds: The following classes of compounds with respect to their IUPAC / systematic nomenclature, industrial [wherever applicable] & laboratory methods of preparations, physical properties & chemical reactions with emphasis on reaction mechanisms [arrow based] & stereochemistry [wherever applicable].

Aromatic hydrocarbons: Phenolic compounds. Aromatic & aliphatic amines. Diazonium salts. Aromatic nitro - compounds, aryl halides, & ethers.

Polycyclic aromatic hydrocarbons: Syntheses & reactions with mechanisms of bi & tricyclic fused carbocyclic rings like naphthalene, anthracene, & phenanthrene.

Carbonyl chemistry: Carbonyl chemistry involving group conversions & their reaction mechanisms along with stereochemistry wherever applicable: Wolf-Kishner reduction, Michael addition / 1,4-addition / conjugate addition, Mannich condensation / reaction, Beckmann rearrangement, Baeyer Villiger rearrangement, Curtius, Wolff, & Lossen rearrangements, Pinacol-pinacolone rearrangement etc

Heterocyclic chemistry; IUPAC Nomenclature of heterocyclic rings [3-10 membered] containing O, S, & N atoms. Nomenclature of above rings containing mono-, di-, & multiple [same or different] heteroatoms should also be covered. Nomenclature of 2 & 3 fused rings containing mono-, di-, & multiple heteroatoms [same or different] should also be covered. Syntheses & reactions of three to six- membered rings in detail. Syntheses of five & six-membered rings containing mono- or any di- heteroatoms [O, S, & N]. Syntheses of quinoline, isoquinoline, benzoxazole, benzothiazole, & benzimidazole, benzotriazole, and benzothiazole.

Stereochemistry: Stereochemistry definition, Chirality & asymmetry [introduction of the same to S, P, & N]. Definition & classification [different types of isomerisms]. Enantiomers, diastereomers. Enantiomerism & diastereomerism. Meso compounds & their optical activity. Stereochemistry in acyclic compounds. Newman projection formulae & their significance. Conformational analysis of n- butane. Absolute & relative configuration. Assigning R & S configuration based on Cahn Ingold & Prelog system. Racemic mixture- its definition & resolution. Definitions of terms stereoselective, stereospecific, Enantiomeric excess & diastereomeric excess. Stereochemistry in cyclic systems. Conformations of cyclohexane. Cis-trans relationship in cyclohexane. Prediction of stability of different conformations of 1, 2- 1,3- & 1,4- disubstituted cyclohexanes. Effect of multiple substitutions on the stability of cyclohexane conformations. Chair conformations of cis-, & trans-decalins, perhydrophenanthrenes, & a tetracyclic steroidal nucleus. An introduction to atropisomerism.

Carbohydrates: Definition & classification. D & L nomenclature in sugars. Different ways of drawing / representing a sugar molecule [including cyclic Structure], interconversion of these representations. Anomers & epimers. Mutarotation. Reactions of glucose. Chain extension & chain reduction of a sugar.

Amino acids & proteins: Amino acids & proteins. Definition & classification. D & L Amino acids, natural, essential, & non-essential amino acids. Denaturation, Strecker, Gabriel phthalimide methods for the preparation of amino acids. Peptide bond & its formation. Two protective groups each, for -NH2 & -COOH functionalities during protein synthesis. Sequencing of a protein by chemical & enzymatic methods.

Pericyclic reactions: Pericyclic reactions. Concept of HOMO & LUMO. Drawing of HOMO & LUMO of 1, 3-butadiene, allylic cation, radical & anion, & 1, 3, 5-hexatriene, Diel's-Alder & retro Diel's Alder reaction.

Pharmaceutical impurities: Impurities in pharmaceutical substances, sources, types & effects of impurities. Limit tests for heavy metals like lead, iron, arsenic, mercury & for chloride & sulphate as per Indian Pharmacopoeia [I. P.].

Monographs: Monograph & its importance, various tests included in monographs as per I. P. A study of the following compounds with respect to their methods of preparation, assay, & pharmaceutical uses of sodium citrate, calcium carbonate, copper sulphate, light & heavy kaolin, ammonium chloride & ferrous gluconate.

Isotopes: Isotopes - stable & radioactive, mode & rate of decay. Types & measurement of radioactivity. Radiopharmaceuticals & their diagnostic & therapeutic applications in pharmacy & medicine - such as 125 I, 32P, 51Cr, 60Co,59 Fe, 99 Tc-M. Radiocontrast media, use of BaSO4 in medicine.

Dentifrices, desensitizing agents, & anticaries agents

Therapeutic classes of drugs: The following topics should be dealt with covering nomenclature [including stereochemical aspects], biological activity [including side & toxic effects], mode of action, structure-activity relationship [where ever applicable] & syntheses of reasonable molecules, 1. General anesthetics, 2. Local anesthetics, 3. Diagnostic agents. 4. Coagulants, anticoagulants & plasma expanders. 5. Antiseptics, disinfectants, sterilants, & astringents. 6. Purgatives, laxatives & antidiarrhoeal agents.

Various classes of therapeutic agents: A detailed study of the following classes with respect to drug nomenclature, classification, physicochemical properties, mode of action [MOA], structure-activity relationships [SAR], wherever applicable, synthesis of simple & prototype molecules, drug metabolism, therapeutic uses & side effects. Drug resistance, wherever applicable, should be covered in respective classes of drugs: Antimalarials, Antiamoebic agents,Anthelmintic agents, Antibacterial sulpha drugs [only], Quinolone antibacterials, Antimycobacterial drugs, Antifungal agents, Antiviral agents including HIV & anti-HIV drugs, Thyroid & antithyroid drugs, Antiallergic agents, Antiulcer agents & Proton Pump Inhibitors, Hypoglycemic agents etc

Different classes of therapeutic drugs: A detailed study of the following classes with respect to drug nomenclature, classification, physicochemical properties, mode of action [MOA], structure-activity relationships [SAR], wherever applicable, synthesis/biosynthesis of simple & prototype molecules, drug metabolism, therapeutic uses & side effects. Drug resistance, wherever applicable, in respective classes of drugs. a) Sedative-hypnotics b. Antiepileptic agents. c. Neuroleptics. d. Anti-anxiety drugs. b) Antibiotics. Penicillins, cephalosporins & other beta-lactam antibiotics like imipenem & aztreonam. Beta-lactamase inhibitors such as clavulanic acid & sulbactam. Chloramphenicol. Tetracyclines. Aminoglycoside antibiotics. Macrolide antibiotics. Lincomycins. Polypeptide antibiotics. Anticancer antibiotics. III. Steroids. Corticosteroids [gluco- & mineralocorticoids] & anti-inflammatory steroids. Sex steroids. Male & female contraceptive agents. Anabolic steroids.Anticancer agents. c) Narcotic [centrally acting] analgesics [analgetics]. Morphine & all its structural modifications [peripheral & nuclear]. Narcotic agonists & antagonists [dual & pure]. Non-narcotic analgesics [NSAIDS]. Difference between narcotic & non-narcotic agents d) Adrenergic drugs. Neurotransmitters & their role. General & specific adrenergic agonists & antagonists [up to alpha-2 & beta-2 only] e) Cholinergic agents. Muscarinic & nicotinic cholinergic agonists & antagonists [up to M2 & N2]. Neuronal [transmission] blockers. f) Drugs used in neuromuscular disorders. Drugs used in the treatment of Parkinson's disease. Central & peripheral muscle relaxants g) Hypertensive, antihypertensive, & antianginal agents. h) Diuretics. i) Eicosanoids. Prostaglandins, prostacyclins, & thromboxanes. Their biochemical role, biosynthesis, & inhibitors.

Introduction to quantitative structure-activity relationship. [QSAR]: Linear free energy relationship. Hammett's equation. Use of substituent constants such as π, σ, Es, & physicochemical parameters such as pKa, partition coefficient, Rm, chemical shifts, molar refractivity, simple & valance molecular connectivity to indicate electronic effects, lipophilic effects, & steric effects. Introduction, methodology, advantages & disadvantages/limitations of Hansch analysis.

Combinatorial chemistry: Introduction & basic terminology, methods and applications. Limitations of combinatorial synthesis. Introduction to throughput screening.