04_P016_24030

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“SYNTHESIS AND ANTIMICROBIAL EVALUATION OF NOVEL SUBSTITUTED

DERIVATIVES OF GALLIC ACID”

DISSERTATION PROTOCOL

Submitted to the

RAJIV GANDHI UNIVERSITY OF HEALTH SCIENCE, KARNATKA,

BANGALORE

BY

J.S. ABINESH DEVARAPU

M.PHARM, PART-1

DEPARTMENT OF PHARMACEUTICAL CHEMISTRY

UNDER THE GUIDANCE OF

Mr. M. GURUMURTHY, M.PHARM

Associate professor Department of pharmaceutical chemistry

Dr. H.L.T. College of pharmacy,

Kengal, Channapatna – 562 161

Ramanagaram dist.

2010

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RAJIV GANDHI UNIVERSITY OF HEALTH SCIENCES, KARNATAKA

BANGALORE

ANNEXURE II

PROFORMA FOR REGISTRATION OF SUBJECT FOR DISSERTATION

1 Name of the Candidate and address:

J.S.ABINESH DEVARAPU

Dr. H.L T.COLLEGE OF PHARMACY,

KENGAL, CHANNAPATNA,

RAMANAGARAM DIST. 562 161.

2 Name of the Institute:Dr. H.L.T. College of Pharmacy

Kengal Channapatna – Ramanagaram Dist.

3 Course of the study and subject:Master of Pharmacy in Pharmaceutical Chemistry.

4 Date of admission to the course:16/11/2010

5 Title of Topic:“SYNTHESIS AND ANTIMICROBIAL

EVALUATION OF NOVEL

SUBSTITUTED DERIVATIVES OF

GALLIC ACID”

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6. Brief resume of the intended work

6.1: Need for the study:

Various substituted Gallic acid (a strong natural antioxidant1) derivative have been found to possess w

spectrum of biodynamic properties such as Antimicrobial2, Antitubercular 3, Antiviral (rabies virus)4, A

inflammatory5, Antitumour 6, Plant growth promoter 7, Insecticidal activity8 , Radical scavenging activities and A

allergic properties. The chemistry of these substituted derivatives of Gallic acid has been the fascinating fiel

investigation in medicinal chemistry, as it has been found to exhibit enhanced biological profile.

There is another derivative in the field of the investigation i.e. Schiff base derivative, derived from arom

amines and aromatic aldehyde, (R 2C=NR ′, azomethine), which has been reported to possess wide spectrum

activities such as Antimicrobial 9, Anti Hypertensive 10, as a fluorescent indicator.

In view of the above observation, it was thought worth-while to synthesize a new Schiff base derivative w

Gallic acid molecule in which it is linked with the different aromatic amine and further investigate these compo

for their Antibacterial and antifungal activities.

The present work has been directed to synthesize various substituted Schiff base derivative of Gallic

through mild and facile synthetic route and also the study has focused on the influence of the various substitu

on Antimicrobial spectrum of substituted Gallic acid.

6.2 Review of literature:

The review of various published work related to subject revealed the following:

1. Pharmacognosy1, Nirali Prakashan, 19th edition , C.K. KOKATE, page no. 256.

2. S.Arunkumar et al 2, has synthesized a series of 2-(3,4,5-trihydroxy phenyl)-5-aryl-1, 3,4- oxadiazole

synthesized from propyl gallate and hydrazine hydrate in presence of ethanol to give 3, 4

trihydroxybenzohydrazide followed by reaction with phosphorus oxychloride and various aromatic a

and the synthesized compound were tested against bacteria and fungi.

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3. K Ilango et al 3, has Synthesized a series of novel 4-aryl-3-chloro-N-(3,4,5-trihydroxy benzamido

azetidinones, were synthesized by reacting various Schiff bases of galloyl hydrazide, with chloroac

chloride in the presence of dioxan and triethylamine.and studied their antitubercular activity.

4. Juliana H. Cha´vez et al 4, has studied antiviral activity of phenolic compounds and derivatives aga

rabies virus.

5. Arunkumar Subramani et al 5, has Synthesized new series of 5-{6-(substituted phenyl)-5,6-dihydro-(1,

triazolo(3,4-b) (1,3,4)thiadiazol-3-yl}benzene-1,2,3-triol have been synthesized. The reaction of Pr

gallate and hydrazine hydrate yielded galloylhydrazide ,which on treatment with potassium hydroxide

carbondisulfide furnished 5-(-5-mercapto-1,3,4-oxadiazol-2-yl) benzene-1,2,3-triol .This on hydrazinol

gave 5-(4-amino-5mercapto - 4H-1,2,4 – triazol-3-yl) benzene -1,2,3-triol. Finally cyclization of

various aromatic aldehyde and piperidine converted into novel triazolo, thiadiazole derivatives of g

acid and studied anti inflammatory activity.

6. Yi-Chen Chia et al 6, has studied that Extract of Toona sinensis (TS ) have effects on on various human

squamous carcinoma cell lines (HOSCC), including UM1, UM2, SCC-4, and SCC-9. cultured cell li

including anti-proliferative activity in cancer cells.

7. Arvind Singh Negi et al 7, has modified Gallic acid to naphthophenone derivatives with esterified fatty

side chain. an ethyl crotonate ester of naphthophenone derivative has shown potent auxin like gro

promoter activity.

8. Xi iu-Fang Cao et al 8, has Synthesized a series of novel β-lactams derived from natural gallic acid w

conveniently synthesized via classical Staudinger ketene-imine cyclo addition reaction. The prelimin

bioassay showed that some of the target compounds exhibited obvious insecticidal activity against Helio

armigera at the dosage of 0.2 mg/mL.

9. Santosh Kumar et al 9, has Synthesized the various Schiff base derivative from different substit

aromatic aldehyde as a starting material for Schiff base with sulfonamide in presences of alcohol and ac

reagent and studied antimicrobial activity.

10. M.T. Shreenivas et al 10, has synthesized Schiff bases, by condensation reaction of nitro compo

containing biphenyl ether amines with aromatic aldehydes and ketone derivatives and thiazolidines w

prepared by Schiff base with thioglycolic acid and the synthesized compounds were screened for A

Angiotension (AT II) Receptor Antagonist activity.

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6.3 Main objectives of the study:

The present work is an attempt to

1. Synthesize a novel substituted Gallic acid derivative by using substituted Phenol, Thionyl chlor palladium catalyst, Ammonia, LiAlH4,Various Aromatic Aldehyde, Aromatic amines etc.

2. Characterize, identify, and purify the synthesized compound by spectroscopy like UV, IR, 1HNMR

chromatographic studies like TLC and melting point and boiling point determination.

3. Screening the active compound for antimicrobial activities by like cup plate method, strip-plate met

etc using gram +ve and gram-ve bacteria, fungus etc.

7. Materials and methods:

7.1 Source of Data:

The preliminary data required for the experimental study was obtained from

1. CD – Rom search available at National Center for Scientific information (NCSI) IISc Bangalore.

2. Chemical Abstract.

3. Journals.

4. Dr. H.L.T. College of Pharmacy library.

5. Relevant books.

6. Internet sources.

7. The data will be collected by laboratory investigation and will be recorded.

7.2 Methods of collection of Data (including sampling procedure if any):

Data pertaining for the present study will be obtained from Extensive literature survey, carried out us

laboratory of Dr. H.L.T. College of pharmacy, R.G.U.H.S Bangalore, and visiting various website through

internet.

The experimental data would be obtained from the various techniques adopted in the synthesis and activit

Gallic acid and Other Schiff base derivatives published in various national and international journals.

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As per the literature review, the newer Gallic acid will be synthesized and

Progress of reaction as follows:-

GALLIC ACID

SOCl2

Reflux

3,4,5- Tri hydroxybenzoyl chloride

NH3

3,4,5- Tri hydroxy benzamide

LiAlH4

3,4,5- Tri hydroxy benzylamine

Aromatic aldehyde

reflux 6hr/ C2H5OH

H2/ Pd 3,4,5-Tri hydroxybenzaldehyde

Aromaticamines

reflux 6hr /

C2H5OH

1-( substituted phenyl imine)pyrogallol

BaSo4

N- substituted benzyl derivative

SCHEME OF SYNTHESIS

7.3 Does the study require any investigation to be conducted on patient or other human beings

animals? If so please describe briefly.

-- NOT APPLICABLE --

7.4 Has ethical clearance been obtained from your institute in case of 7.3?

-- NOT APPLICABLE --

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8. List of References:

1. Pharmacognosy , Nirali Prakashan, 19th edition , C.K. KOKATE, page no. 256.

2. S.N. Sawney, S.P. Singh and O.P. Bansal, Indian journal of heterocyclic chemistry, 2001; 44B: 125-126.

3. K Ilango and S Arunkumar, Tropical Journal of Pharmaceutical Research, 2011; 10 (2): 219-229.

4. Juliana H. Cha´vez , Paulo C. Leal , Rosendo A. Yunes , Ricardo J. Nunes , Veterinar

Microbiology, 2006;116: 53–59

5. Arun kumar Subramani, Ilango Kaliapan, Ravindar Bairam, Ramalakshmi N. Der Pharma Chemica; 2009,

(1):70-77 .

6. Yi-Chen Chia 1, Ranjan Rajbanshi 2, Colonya Calhoun 2 and Robert H. Chiu. Molecules; 2010: 15, 8377-

8389.

7. Arvind Singh Negi, Mahinder P. Darokar, Sunil K. Chattopadhyay, Bioorganic & Medicinal Chemistry

Letters, 2005;15: 1243–1247.

8. Xiu-Fang Cao, Yun-Shen Wang, Shao-Wei Li, Chang-Shui Chena and Shao-Yong Ke. Journal of the Chin

Chemical Society; 2011: 58, 35-40.

9. Santosh Kumar, Niranjan M S, Chaluvaraju K C, Jamakhandi C M and Dayanand Kadadevar, Journal of

Current Pharmaceutical Research; 2010: 01, 39-42.

10. M.T. Shreenivas, B.P Chetan and A.R.Bhat, Journal of Pharmaceutical Science and Technology ; 2009:1

88-94.

11. Sudeep Mandal, Dibyajyoti Saha, Bindu Jain and Vibhor K Jain. International Journal of Research

Pharmaceutical and Biomedical Sciences; 2011: 2 (1), 168-174.

12. S. Arunkumar, k. Ilango, r. S. Manikandan and n. Ramalakshmi. E-Journal of Chemistry; 2009: 6(S1), S

S128.

13. Sang-Hyun Kim,Chang-Duk Jun, Kyongho Suk, Byung-Ju Choi. Toxicological Sciences; 2006: 91(1), 1

131.

14. Vandana Srivastava, Hari Om Saxena, Karuna Shanker. Bioorganic & Medicinal Chemistry Letters; 2006:

4603–4608.

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09 Signature of candidate:

10 Remarks of the Guide:

Topic selected for Dissertation work issatisfactory. This can be carried out in our

Laboratory.

11 Name and designation of (in block letters)

11.1. Guide:

Mr. M. GURUMURTHY, M.PHARM.

ASSOCIATE PROFESSOR DEPT.OF PH. CHEMISTRY

DR. H.L.T. COLLEGE OF PHARMACY

KENGAL, CHANNAPATNA – 562 161,RAMANAGARAM DIST.

11.2 Signature:

11.3 Co – guide (if any) --

11.4 Signature --

11.5 Head of department:

Mr. M GURUMURTHY, M.PHARM.ASSOCIATE PROFESSOR DEPT.OF PH. CHEMISTRY

DR. H.L.T. COLLEGE OF PHARMACY

KENGAL, CHANNAPATNA – 562 161,RAMANAGARAM DIST.

11.6 Signature:

12 12.1 Remarks of the chairman andPrincipal: The above mentioned information is correctand recommends the same for approval.

12.2 Signature:

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From

J.S.ABINESH DEVARAPU

M.Pharm, Dept. of pharmaceutical chemistry,

Dr.H.L.T. College of pharmacy,Kengal, Channapatna.

To

The Registrar (Evaluation)

Rajiv Gandhi University of Health Science,4th “T” Block, Jayanagar,

Bangalore- 560041.

(Through proper Channel)

Respected sir,

Sub: Submission of Synopsis of Dissertation

Herewith, I am submitting of dissertation work “SYNTHESIS AND ANTIMICROBIAL EVALUATI

OF NOVEL SUBSTITUTED DERIVATIVES OF GALLIC ACID” for registration in M.Ph

(Pharmaceutical Chemistry) of Rajiv Gandhi university of Health science, Bangalore, Karnataka.

Kindly accept the same and oblige.

Thanking you,Yours faithfully,

Place: Channapatna (J.S.ABINESH DEVARAPU)

Date:

Guide:

Mr. M. GURUMURTHY, M. PHARM. PRINCIPAL

Associate Professor Dr. H.L.T. College of PharmacyDept. of Pharmaceutical Chemistry Kengal, Channapatna-562 161

Dr. H.L.T. College of pharmacy Ramanagaram District

Kengal, Channapatna-562 161.Ramanagaram District

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