SYNTHESIS OF PRODRUG OF ESTERS AND AMIDE LINKAGES OF NSAID HAVING CARBOXYLIC ACID, PHENOLIC AND IMINO GROUPS
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1 WRLD JURNAL F PHARMACY AND PHARMACEUTICAL SCIENCES Sen et al. SJIF Impact Factor Volume 5, Issue 11, Research Article ISSN SYNTHESIS F PRDRUG F ESTERS AND AMIDE LINKAGES F NSAID HAVING CARBXYLIC ACID, PHENLIC AND IMIN GRUPS Jalpa G. Patel and Prof. Dr. Dhrubo Jyoti Sen* Department of Pharmaceutical Quality Assurance and Pharmaceutical Chemistry, Shri Sarvajanik Pharmacy College, Gujarat Technological University, Arvind Baug, Mehsana , Gujarat, India. Article Received on 12 Sept. 2016, Revised on 02 ct 2016, Accepted on 23 ct 2016 DI: /wjpps *Corresponding Author Prof. Dr. Dhrubo Jyoti Sen Department of Pharmaceutical Quality Assurance and Pharmaceutical Chemistry, Shri Sarvajanik Pharmacy College, Gujarat Technological University, Arvind Baug, Mehsana , Gujarat, India. ABSTRACT Ibuprofen, Diclofenac & Paracetamol have been taken as NSAID and three prodrugs have been synthesized by reacting of acid chloride of ibuprofen & diclofenac with paracetamol to get prodrug of ester linkage and acid chloride of ibuprofen has been reacted with diclofenac to get prodrug of amide linkage. These have been characterized by IR and authenticated by m.p. and logp values. KEYWRDS: Ibuprofen, Diclofenac sodium, Paracetamol, Thionyl chloride, Peptoid, logp, pka, Melting Point, Prodrug. INTRDUCTIN Ibuprofen [C 13 H 18 2 ; MW=206] (2 [4 (2 methylpropyl)phenyl] propanoic acid), from isobutylphenylpropanoic acid, is a drug in the nonsteroidal anti inflammatory drug (NSAID) class used for treating pain, fever, and inflammation. logp=3.97, pka=4.91. Ibuprofen m.p.=theoretical (76 C), practical (75 C). [1-3] Diclofenac sodium [NaC 14 H 10 2 N; MW=302] (Sodium {2 [(2,6 dichlorophenyl)amino] phenyl}acetic acetate) is a nonsteroidal anti inflammatory drug (NSAID) taken or applied to reduce inflammation and as an analgesic reducing pain in certain conditions. logp=4.51, pka=4.15. Diclofenac sodium m.p.=theoretical ( C), practical (282 C) Paracetamol [C 8 H 9 N 2 ; MW=151] (N (4 hydroxyphenyl)acetamide), also known as acetaminophen or APAP, is a medication used to treat pain and fever. logp=0.46, pka=9.38. Paracetamol m.p.=theoretical (169 C), practical (170 C). Vol 5, Issue 11,
2 Ibuprofen, Diclofenac and Paracetamol all comes under NSAID and all three are acidic in nature. Ibuprofen and diclofenac both have free carboxylic acid ( CH) group and paracetamol has free phenolic group ( H). The idea of formation of prodrug by joining of free carboxylic acid ( CH) group of ibuprofen and diclofenac with phenolic group ( H) of paracetamol by converting free carboxylic acid ( CH) group into acid chloride ( C) and conjugated with free phenolic group ( H) by benzoylation reaction to get the three desired compounds [Prodrug A & Prodrug B having ester ( C ) linkage. Acid chloride ( C) of ibuprofen when reacts with imino group ( ) of diclofenac then it produces Prodrug C having amide ( C ) linkage. [4-6] H 3 C H 3 C S 2 H 2-[4-(2-methylpropyl)phenyl]propanoic acid 2-[4-(2-methylpropyl)phenyl]propanoyl chloride H 3 C 2-[4-(2-methylpropyl)phenyl]propanoyl chloride + H N-(4-hydroxyphenyl)acetamide H 3 C Prodrug-A Figure 1: Prodrug of Ibuprofen & Paracetamol. Vol 5, Issue 11,
3 Na S 2 sodium {2-[(2,6-dichlorophenyl)amino]phenyl}acetate {2-[(2,6-dichlorophenyl)amino]phenyl}acetyl chloride + {2-[(2,6-dichlorophenyl)amino]phenyl}acetyl chloride H N-(4-hydroxyphenyl)acetamide Prodrug-B Figure 2: Prodrug of Diclofenac sodium & Paracetamol. H 3 C H 3 C S 2 H 2-[4-(2-methylpropyl)phenyl]propanoic acid H 3 C 2-[4-(2-methylpropyl)phenyl]propanoyl chloride 2-[4-(2-methylpropyl)phenyl]propanoyl chloride + H {2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid H 3 C N H Prodrug-C Figure 3: Prodrug of Ibuprofen & Diclofenac. Vol 5, Issue 11,
4 Chemistry: Ibuprofen (2g, 0.01m) has been reacted with 5ml thionyl chloride and refluxed for 30mins in moisture free environment until all ibuprofen has been dissolved. The reaction mixture was heated on water bath to remove excess thionyl chloride. It was then cooled in ice and paracetamol (1.5g, 0.01m) dissolved in methanol was added in it with shaking. ily droplets separates out which was then mixed with ice water and kept in ice to solidify the droplets into white solid of prodrug A. It was filtered and %yield and m.p. has been recorded for dried mass. Prodrug A is a combination of ibuprofen (logp=3.97, nonpolar) and paracetamol (logp=0.46, polar) produced a derivative of semipolar unit (logp=4.56). MP= C. %yield= Prodrug A [4 (acetylamino)phenyl (2S) 2 [4 (2 methylpropyl) phenyl] propanoate]. [Molecular Formula=C 21 H 25 N 3, Formula Weight=339.42]. (Solubility=0.1g soluble in 10ml methanol/10ml acetone). Figure 4: Histogram of logp of prodrugs. Diclofenac sodium (3g, 0.01m) has been reacted with 10ml thionyl chloride and refluxed for 30mins in moisture free environment until all diclofenac sodium has been dissolved. The reaction mixture was heated on water bath to remove excess thionyl chloride. It was then cooled in ice and paracetamol (1.5g, 0.01m) dissolved in methanol was added in it with shaking. ily droplets separates out which was then mixed with ice water and methanol and kept in ice to solidify the droplets into white solid of prodrug A. It was filtered and %yield and m.p. has been recorded for dried mass. Prodrug B is a combination of diclofenac sodium (logp=6.13, nonpolar) and paracetamol (logp=0.46, polar) produced a derivative of semipolar unit (logp=4.9). MP= C. %yield= The beauty of reaction shows that Vol 5, Issue 11,
5 diclofenac sodium which is sodium salt that releases free diclofenac during reaction between thionyl chloride in acid environment to get free CH group which then reacts with thionyl chloride to produce acid choride [ C] which then combines with phenolic group [ H] of paracetamol to give Prodrug B [4 (acetylamino)phenyl {2 [(2,6 dichlorophenyl) amino]phenyl}acetate]. [Molecular Formula=C 22 H 18 2 N 2 3, Formula Weight=429.29]. (Solubility=0.1g soluble in 10ml methanol/10ml acetone). [7-9] Figure 5: Histogram of molecular weights of prodrugs. Ibuprofen, diclofenac sodium and paracetamol all are white in colour. Prodrug A [Ibuprofen & Paracetamol] produces off white product. Prodrug B [Diclofenac & Paracetamol] produces dark brown product. Prodrug C [Ibuprofen & Diclofenac] produces light brown product after keeping in refrigerator overnight after addition of ethanol. Prodrug C [N (2,6 dichloro phenyl) [2 ({(2S) 2 [4 (2 methylpropyl)phenyl]propanoyl}amino)phenyl] acetic acid]. MP= C. %yield= (Solubility=0.1g soluble in 10ml methanol/10ml acetone). [Molecular Formula=C 27 H 27 2 N 3, Formula Weight =484.41]. This is due to formation of amide linkage ( C ) because ester linkage ( C ) produced the products prodrug A & prodrug B within an hour. The linkage ( C X ; X=/) shows the electronegativity (=3.44 and N=3.04); so ester ( C ) forms faster than amide ( C ) because =3.44 > N=3.04. (Vogel, 1956) Vol 5, Issue 11,
6 Figure 6: Ibuprofen spectral datas H 3 C H Vol 5, Issue 11,
7 IR (cm 1 ; ν): CH: (1721) CH( ): / Methyl C..H asym./sym. stretch (2980), / gem Dimethyl or iso (doublet) (1380), / Methyl C..H asym./sym. bend (1420) C=C C Aromatic ring stretch (1510) NMR (ppm): (s, CH), 7.48 (s, Ar H), 3.83 (d, Ar CH ), 2.48 (d, Ar CH 2 ), 1.5 (d, CH( ) 2 ) Mass Spectrum: m/e=206 (M+) [fragments=44, 134] Figure 7: Diclofenac sodium spectral datas Vol 5, Issue 11,
8 Na IR (cm 1 ; ν): C Aliphatic chloro compounds, (745), C stretch Carboxylic acid (1720) 3450 Aromatic secondary amine, (3440), stretch C=C C Aromatic ring stretch (1573) NMR (ppm): 7.58 (d, Ar) Mass Spectrum: m/e=296/298 (M+2) [318 for sodium salt] Figure 8: Paracetamol spectral datas Vol 5, Issue 11,
9 H IR (cm 1 ; ν): 1200 Phenol, C stretch (1200), Phenols, H stretch (3630) Amide (1680) Ketone (1720) / Methyl C H asym./sym. stretch (2870) C=C C Aromatic ring stretch (1580) NMR (ppm): 7.45 (d, Ar), 6.93 (Ar CH ), 9.43 ( H), 10.1 ( ), 2.04 ( ) Mass Spectrum: m/e=151 (M+) [fragments=109, 44] H 3 C Prodrug=A (MW=339) Prodrug=B (MW=429) Vol 5, Issue 11,
10 H 3 C N H Prodrug=C (MW=484) Figure 9: Prodrug and 3D structures CNCLUSIN Three prodrugs (Prodrug A, Prodrug B and Prodrug C) have been successfully synthesized and have shown different melting points from individual parent drugs (Ibuprofen, Diclofenac sodium and Paracetamol) which indicate the authenticity of fulfillment of prodrug synthesis. IR spectra of Prodrug-C proves the linkage of amide ( C ) formed by acid chloride ( C) of ibuprofen with imino ( ) of diclofenac. Vol 5, Issue 11,
11 H 3 C N Prodrug-C: IR (cm 1 ; ν): Amide ( C ): (standard= , found=1735), Ketone (>C=): (standard= , found=), Tertiary amino (Peptoid, =N ): (standard: , found=1192), Chlorine ( ): (standard= , found=747, 778), Phenyl ( C6H5): (standard= , found=1577), Carboxylic acid ( CH): (standard= , found=1734), Methyl (CH3 ): (standard= / , found=2952) Methyl C H asym./sym. stretch standard= / , found=1447). Actually Prodrug-A and Prodrug-B both are peptide [ C ] in nature where as Prodrug-C is peptoid in nature [ CN (Ar) ] because amide group is free in Prodrug-A and Prodrug-B to make peptide but hydrogen of amide in Prodrug-C is replaced by aryl ring to make peptoid. H Their solubility parameters also found different from parent drugs. Prodrug is a substance having no medicinal importance but after biotransformation in GIT it releases the parent drug which is able to show the pharmacological activity. ur future goal is to perform in-vitro biotransformation of these prodrugs by acidic and alkaline hydrolysis of both ester ( C ) and amide ( C ) linkages into free drugs and chromatographically separation of their Rt in HPLC. Study of in-vitro biotransformation of prodrugs of ester and amide linkages of ibuprofen, diclofenac sodium and paracetamol in acidic and alkaline medium will be our next target after this project. REFERENCE 1. A.V. Bhosale, G.P. Agrawal and P.Mishra: Preparation and Evaluation of Directly Compressible Forms of Mutual Prodrugs of Ibuprofen Forms of Mutual Prodrugs of Ibuprofen. Indian Journal of Pharmaceutical Sciences, 2006; 68(4): B.C. Ghodeswar, R.N. Pophalikar, M.R. Bhojani, D. Nagpal and S. Dhaneshwar, Indian Journal of Pharmaceutical Sciences., 2004; 66: K. Koren, A.R. Mann, A.L. Colosimo, Z. Diaz, A. Nuclelman, I. Levovich, Y. Jing, S. Waxman and W.H. Miller, Jr., Mol. Cancer Res., 2003; 1: Vol 5, Issue 11,
12 4. J.E. Slemmer, B.R. Martin and M.I. Damaj. Bupropion is a nicotinic antagonist. J. Pharm. Exp. Ther., 2000; 295: C. Wu, J. Quan, J. Xie, C Branford-White, L. Zhu, Y. Yu and Y. Wang. Preparation and controlled release of degradable polymeric ketoprofen-saccharide conjugates. Polym Bull., 2011; 67: M, Babazadeh and T. Mosanejhad, Vinyl ester type polymers containing ibuprofen pendents: synthesis, characterization and evaluation. Iran Polym J., 2009; 18: L. Shargel, Susanna Wu-Pong and B.C. Andrew, Applied Biopharmaceutics & Pharmacokinetics, 6 th Ed.McGraw-Hill Medical Publishing Division, US., 2012; 47-66, S. Shirke*, S. Shewale and M. Satpute, Prodrug design: an overview. International Journal of Pharmaceutical, Chemical and Biological Sciences., 2015; 5(1): A.I. Vogel, A textbook of practical organic chemistry, 3 rd edition, Longmans, Green and Co, Ltd, London, 1956; 791: Vol 5, Issue 11,
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