MEDICINAL CHEMISTRY- III Lecture 2 Wed. 16/ 5/ 1432H Prof. Dr. Wafaa Zaghary.

Slides:



Advertisements
Similar presentations
Obat anti inflamasi non steroid
Advertisements

Anti-Ulcer Agents Michael Alwan November 11, 2004
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 19 Carbonyl Compounds III Reactions at the  -Carbon.
Fragmentation of Amines in EI-MS α-cleavage liberation of neutral molecules (alkenes) from iminium ion involves H-rearrangement (R must be C 2 or longer)
The functional group of a carboxylic acid is a carboxyl group
Chapter 11 Introduction to Organic Chemistry
Chapter Sixteen Carboxylic Acids, Esters, and Other Acid Derivatives.
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 14 Carboxylic.
14.6 Amides Tylenol, an aspirin substitute, contains acetaminophen. Acetaminophen is an amide. It acts to reduce fever and pain; however, it has little.
Anti-Inflammatory Agents ESAT 4001 Pharmacology in Athletic Training.
CHAPTER 21 PHENOLS AND ARYL HALIDES NUCLEOPHILIC AROMATIC SUBSTITUTION
Non Steroidal Anti Inflammatory Drugs, Nonopioid Analgesics By S.Bohlooli, PhD.
Propionic acid derivatives Ibuprofen, naproxen, fenoprofen, flurbiprofen, oxaprozin,→ anti-inflammatory, analgesic, and antipyretic.  These drugs are.
Functional Groups Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 1.
Optimizing Target Interactions
Chapter 13: Aldehydes and Ketones
CH 20: Carboxylic Acids and Nitriles Renee Y. Becker CHM 2211 Valencia Community College 1.
Chemistry 2100 Chapter 19.
PHC 222 Part(I) Dr. Huda Al Salem
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Reactions of Aldehydes and Ketones.
Session III of TIP 1 TIP 2009 Gephart.  The synthesis of ibuprofen was originally reported in 1964 from p-isobutylacetophenone, but the drug was not.
Michelle Fisher. Ibuprofen is used for the treatment of mild to moderate pain, inflammation and fever caused by many and diverse diseases.
TOPIC 11 – ORGANIC CHEMISTRY. TOPIC 11 – Regents Review Organic compounds consist of carbon atoms bonded to each other in chains, rings, and networks.
Organic chemistry Assistance Lecturer Amjad Ahmed Jumaa  Effect of substituents on acidity.  Basicity of aliphatic and aromatic amines.
Chapter 11 Introduction to Organic Chemistry: Alkanes
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction.
Carboxylic Acids And Their Derivatives
Aromatic Carboxylic Acid 1 Dr Md Ashraful Alam 2 A carboxylic acid Contains a carboxyl group, which is a carbonyl group (C=O) attached to a hydroxyl.
MEDICINAL CHEMISTRY-III
Carboxylic acids, esters, and other acid derivatives Chapter 16.
MEDICINAL CHEMISTRY-III
Functional Groups. An atom or group of atoms on a molecule that always reacts in the same manner.
Chem 341 Review for Finals Structure Determination NMR –Chemical shifts, splitting patterns, integrations IR –ROH, C=O Formula => # of Rings + Pi-Bonds.
Aromatic Compounds. Aromatic Systems are Characterized by Their Chemical Stability Note the chemical stability of the aromatic systems to the reaction.
Pharmaceutical Chemistry II Lecture 5 - NSAIDS
Pharmaceutical Chemistry II Lectures 8 & 9 - NSAIDS Joseph O. Oweta | PHC 3201.
Pharmaceutical Chemistry II LectureS 6 & 7 - NSAIDS
Chapter 12. Amines.  Organic derivatives of ammonia, NH 3,  Nitrogen atom with a lone pair of electrons, making amines both basic and nucleophilic 
PAIN MANAGEMENT IN DENTISTRY 1. 2  Pain is defined as an unpleasant sensation that can be either acute or chronic and that is a consequence of complex.
Chapter 12 Amines Suggested Problems: 24-6,30-32,34-5,36,38,50,54.
DRUG DESIGN: OPTIMIZING TARGET INTERACTIONS
Amines
Ch 17- Carboxylic Acids and their derivatives
Organic Chem.
18.5 Amides Tylenol, an aspirin substitute, contains acetaminophen. Acetaminophen is an amide; it acts to reduce fever and pain; however, it has little.
Medicinal chemistry Opiates.
Functional Groups Unit 2.
Functional Groups In an organic molecule, a functional group is an atom or group of atoms that always reacts in a certain way. Section 22-1.
Derivatives of Carboxylic Acids
Functional Groups Unit 3.
Nonsteroidal Anti-Inflammatory Drugs(NSAIDs)
Analgesics.
Amines
2.1 UNSATURATED HYDROCARBONS
Nonsteroidal Anti-Inflammatory Drugs(NSAIDs)
Fundamentals of Organic Chemistry
Fundamentals of Organic Chemistry
Lecture 13: Carboxylic Acids, Esters, Amines and Amides
Fundamentals of Organic Chemistry
CARBOXYLIC ACIDS AND THEIR DERIVATIVES
Carboxylic Acids And Their Derivatives
Organic Chemistry Functional Groups.
Amines Structure Organic derivatives of ammonia, NH3.
Chapter 23: Substituted Hydrocarbons and their Reactions.
By Dr.S.V. Lamture Asso. Prof. &Head Dept of chemistry
Fundamentals of Organic Chemistry
Fundamentals of Organic Chemistry
Fundamentals of Organic Chemistry
Fundamentals of Organic Chemistry
Organic Chemistry CHEM 145
Presentation transcript:

MEDICINAL CHEMISTRY- III Lecture 2 Wed. 16/ 5/ 1432H Prof. Dr. Wafaa Zaghary

III-Anthranilates Flufenamic acid 2—{[3-(Trifluoromethyl)phenyl]amino}benzoic acid. Uses anti-inflammatory

Synthesis

Structure Activity relationships Substitution on the anthranilic acid ring reduce activity. The most active anthranilic acid derivatives have substituents at position 2`,3` and 6`of the ring attached to the anthranilic acid nitrogen. Replacing the –NH- function in fenamic acids produces less active compounds. Thus ether, ketones, and thioether are essentially inactive.

The carboxylic function is required at the 2-position for biological activity. Isomeric 3-carboxy or 4-carboxy derivatives are inactive. A tetrazole function can substitute for carboxylic acid function with retention of anti-inflammatory activity. On the basis of structure-activity relationships for indomethacin and other NSAIDs, and anti- inflammatory receptor site consisting of two non coplaner hydrophobic regions and a cationic centre.

The anti-inflammatory receptor consists of a largely flat area, a trough to accommodate an out-of-plane group (such as an aryl ring acting possibly by charge–transfer type of interaction) and a cationic site to accommodate an acidic anion.

IV-Aryl acetic Acids: Diclofenac Voltaren ® 2-[(2,6-dichlorophenyl)amino]benzene acetic. It is a NSAIDs with balanced cox-1 and cox-2 inhibiting effect.

Indomethacin It is still one of the most potent NSAIDs in use, possessing approximately 25 times the activity of phenylbutazone. It is more potent than aspirin and acetaminophen. CN: 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H- indol-3-acetic acid.

Structure activity relationships All agents posses a centre of activity can be represented by carboxylic acid function, enolic function hydroxamic acid function a sulfonamide or tetrazole. The activity of ester and amide derivatives of carboxylic acid is attributed to the metabolic hydrolysis product. The center of acidity is located on carbon atom adjacent to a flat surface represented by aromatic or heteroaromatic. Increasing the distance to two to three carbons diminish activity.

Derivatives of aryl or heteroaryl acetic or propionic acids are most common. Substitution of methyl group on the carbon atom separating the acid centre from the aromatic ring increase the anti-inflammatory activity. Group larger than methyl decrease activity. A second area of lipophilicity which is generally noncoplaner with aromatic or heteroaromatic ring enhance activity. The lipophilic function may consist of an addition aromatic ring or alkyl group.

V-Aryl propionic Acids Ibuprofen Brufen ® 2-(4-isobutylphenyl)propionic acid It is a NSAID used for the treatment of mild to moderate pain.

VI-Pyrazolinone derivatives Metamizole Novalgin®, Baralgin® It has strong analgesic spasmolytic and antipyretic but no anti-inflammatory properties.

VII-Acidic enolic compounds 1. Pyrazolidine 3,5-diones Oxyphenbutazone Tanderil ® Anti-inflammatory

2. Aryl sulfonamides (oxicames): Piroxicam Anti-inflammatory