Syntheses, characterization and in-vitro antimicrobial activity of new substituted furans and thiophenes



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SYNTHESES, CHARACTERIZATION AND IN-VITRO ANTIMICROBIAL ACTIVITY OF NEW SUBSTITUTED

FURANS AND THIOPHENES”

SYNOPSIS FOR



M.PHARM. DISSERTATION

SUBMITTED TO




RAJIV GANDHI UNIVERSITY OF HEALTH SCIENCES

KARNATAKA

BY

MR. BISWAJEET SAHA ROY

I M.PHARM

DEPARTMENT OF PHARMACEUTICAL CHEMISTRY

PES COLLEGE OF PHARMACY

BANGALORE-560 050

(2012-2014)


RAJIV GANDHI UNIVERSITY OF HEALTH SCIENCES
KARNATAKA, BANGALORE

ANNEXURE-II



PROFORMA FOR REGISTRATION OF SUBJECT FOR DISSERTATION


1.

Name of the candidate and address

MR. BISWAJEET SAHA ROY

Ι. M. PHARM

(PHARMACEUTICAL CHEMISTRY)

PES COLLEGE OF PHARMACY

HANUMANTHANAGAR

BANGALORE-560 050


PERMANENT ADDRESS:

C/O MR. SWAPAN KUMAR SAHA ROY

DB-27 SECTOR I

SALTLAKE


KOLKATA- 700064

WEST BENGAL



2.

Name of the institution

PES COLLEGE OF PHARMACY

HANUMANTHANAGAR

B.S.K.1st STAGE

BANGALORE:-560 050



3.

Course of the study

MASTER OF PHARMACY

(PHARMACEUTICAL CHEMISTRY)




4.

Date of Admission

22nd JUNE 2012

5.

Title of the topic:
SYNTHESIS, CHARACTERIZATION AND IN-VITRO ANTIMICROBIAL ACTIVITY OF NEW SUBSTITUTED FURANS AND THIOPHENES”




6.


BRIEF RESUME OF THE INTENDED WORK
6.1 Need for the study:

Infectious microbial diseases remain pressing problems worldwide, because resistance to a number of antimicrobial agents among variety of clinically significant species of microorganisms (like methicillin-resistant Staphylococcus aureus (MRSA)) has become an important global health problem. Hence, furan and thiophene derivatives have been widely used as antimicrobial agents Prompted by these observations and as part of synthetic effort directed toward the synthesis of antimicrobial agents, various new substituted furans and thiophenes are being synthesized and evaluated.




    1. Review of the literature:


References pertaining to furan:


  1. Mamta Rani et al(1)., reported the synthesis and evaluation of [5-(furan-2-yl)-phenyl]-4,5-carbothioamide-pyrazoline derivatives such as 5-(Furan-2-yl)-3-[2-(benzyloxy) phenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide with antimicrobial action. [2012].



(1)


  1. Jingbao Liu et al(2)., reported the synthesis and antimicrobial activity of 3-methanone-6-substituted-benzofuran derivative.[2012].


R1= 5-methylfuran-2-yl, 4-methoxyphenyl; R2= methyl, furan-2-yl, 4- trifluoromethylphenyl, 3,4,5-trimethoxyphenyl.

(2)


  1. Azar Tahghighi(3) et al., reported the synthesis and anti-leishmanial activity of compounds

having 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines containing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moieties such as N-((1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine.[2012]

(3)


  1. Zhu-Ping Xiao et al(4)., reported the antimicrobial activity of 4-alkoxy-3-arylfuran-2(5H)-ones against Gram-positive bacteria. [2011].



(a) (b)
For (a) R1=R2= -H, -Cl, -F, -Br, OCH3
For(b) R1=R2= -H, -Cl, -F, -Br, OCH3
R3= , , etc.

(4)



  1. Samir Bondock et al(5)., synthesized and studied the in-vitro anti-bacterial action of furo{[2,3c]pyrazoles like (Z)-N-(3-methyl-1-phenyl-1H-furo[2,3-c]pyrazol-4(5H)-ylidene)-1H-benzo[d]imidazol-2-amine. [2011].



(5)



  1. Sahar M. I. Badr et al(6)., synthesized and reported the antimicrobial activity of [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid.[2011]




R= -C2H5, -C6H5, n-C4H9 etc.
(6)


  1. Xizhen Jiang et al(7)., synthesized some novel substituted benzofurans like (4-Hydroxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone having good anti-bacterial activity. [2011].


(7)

  1. Bakr F. Abdel-Wahab et al(8)., reported the synthesis and antimicrobial activity of substituted 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1, 3-thiazol-2-yl]-1H-pyrazoles such as compound a and b respectively.[2009]





  1. (b)

For(a) : Ar = phenyl, 4-chlorophenyl, 4-methoxyphenyl

For(b) : Ar = phenyl, 4-chlorophenyl

Ar1= phenyl, 4-bromophenyl

(8)


  1. Hatem A. Abdel-Aziz et al(9)., synthesized and reported that 2-substituted -3-methylbenzofuran derivatives such as 2-(3-Methylbenzofuran-2-carboxamido)benzoic acid(denoted by a) have good anti-bacterial activity whereas 2-(3-Methylbenzofuran-2-yl)-4H-3,1-benzoxazin-4-one(denoted by b) shows antifungal activity [2009].


(a) (b)
(9)


  1. Cumhur Kirilmis et al(10)., reported the synthesis and antimicrobial activity of dinaphtho[2,1- b]furan-2-yl-methanone oxime and its derivatives. [2009].



R= CH3CO, ClCH2CO, CH3, C2H5, PhCO, etc.
(10)
References pertaining to Thiophenes:


  1. Rushit Kalaria et al(11)., reported the synthesis and antimicrobial activity of substituted tetrahydrothieno[2,3-c]pyridine-2-yl) Schiff base derivatives like (E)-2-(benzylideneamino)-6-tosyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide.[2012]



(11)



  1. Mohammad Asif Iqbal et al(12)., reported the antimicrobial screening of some novel substituted Thiophenes like (E)-2-(4-methoxybenzylideneamino)-N-(furan-2-ylmethyl)-4,5-dimethylthiophene-3-carboxamide.[2012]

(12)



  1. Yerra Rajeshwar et al(13)., reported the antimicrobial activity of Thieno[2,3-d] pyrimidine like (E)-N-(4-chlorobenzylidene)-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine.[2012]




(13)


  1. Aisha S. M. Hossan et al(14)., synthesized and reported the evaluation of pyrimidinone and oxazinone derivatives fused with thiophene ring like 7-(2-Chloro-6-ethoxypyridin-4-yl)-9-(4-chlorophenyl)-2-methyl-4H-pyrido[3',2':4,5]thieno[3,2-d]-[1,3]oxazin-4-one.[2012]

(14)



  1. Nabila Abdelshafy Khedar et al(15)., synthesized bis-[1,3,4]thiadiazoles having thieno[2,3b]thiophene moiety with activity against Gram-positive bacteria.[2012]


R1= Ph, EtOCO, MeCO

R2= Ph, 4-MePh, 4-ClPh

(15)



  1. B.V Guruprasad et al(16)., reported the synthesis and antimicrobial activity of thiophene-2-carboxamides like (Z)-3-chloro-N'-((2-hydroxyquinolin-3-yl)methylene)benzo[b]thiophene-2-carbohydrazide.[2012]



(16)



  1. Hala M. Aly et al(17)., reported the design and synthesis of some new thiophene, thienopyrimidine derivatives of antipyrine as potential antimicrobial agents.[2011]


(17)




  1. Samir Bondock et al(18)., reported synthesis of thiophene derivatives with benzothiazole moiety like 2-amino-N-(benzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide.[2010]


(18)


19. M.A. Gouda et al(19)., reported the synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety.[2010]



(19)

20. A.M. Khalil et al(20)., reported the synthesis and antibacterial activity of some new thiophene derivatives.[2009]


R=COCH3,COOC2H5, CN

(20)

In the view of the above observations it was thought of interest to synthesize and screen some new Furans and Thiophenes for anti-microbial activity.




    1. SCHEMES

      1. SCHEME 1


Synthesis of new substituted furans





      1. SCHEME 2


Synthesis of new substituted thiophenes


6.4 OBJECTIVES OF THE STUDY:

  1. To achieve the syntheses of some new substituted Furans and Thiophenes by adopting established procedures.

2. The purity and progress of the reactions will be monitored by TLC.


3. The purification of the compounds will be carried out by recrystallization using suitable solvents.


  1. To characterize the structures of newly synthesized compounds by UV, IR, NMR, CHN analysis and MASS spectra.




  1. To evaluate the anti-microbial activity of new compounds by standard protocols and to study the structure-activity relationships and to optimize the structure.




  1. To publish the research work in peer reviewed journals.



7.

8.




7.1 MATERIALS AND METHODS:
Chemicals and other reagents will be purchased from standard companies. The progress of the reactions will be monitored by micro thin layer chromatography. The standard protocols will be followed for purification of the products. Structures of the synthesized molecules will be confirmed by the analytical and spectral data. The biological screening results will be used to study structure-activity relationships.
7.2 Sources of data
IISC LIBRARY, BANGALORE

PESCP LIBRARY, BANGALORE

RGUHS DIGITAL LIBRARY (Helinet)

CENTRAL COLLEGE LIBRARY, BANGALORE


7.3 Method of collection of data
Chemical Abstracts, Journals like Indian Journal of Chemistry, Journal of Medicinal Chemistry, Indian Journal of Heterocyclic Chemistry, Journal of American Chemical Society, Indian Journal of Pharmaceutical Sciences, Journal of Organic chemistry, European Journal of Medicinal Chemistry, Bioorganic & Medicinal Chemistry, Journal of Saudi Chemical Society and Turkish Journal of Chemistry, Journal of Applied Technology of Environmental Sanitation.
7.4 Pharmacological Screening:
The evaluation of antimicrobial activity of new substituted furans and thiophenes will be performed using cup plate method.
7.5 Does the study require any investigation or interventions to be conducted on patients or other humans or animals?
-NO-

7.6 Has ethical clearance been obtained from your institution in case of 7.5?

-NOT APPLICABLE-

LIST OF REFERENCES:

1. Rani M, Yusuf M, Khan SA. Synthesis and in-vitro antibacterial activity of [5-(furan-2-yl)-phenyl]-4,5-carbothioamide-pyrazolines. Journal of Saudi Chemical Society. (2012) 16: 431-6.

2. Liu J, Jiang F, Jiang X, Zhang W, Liu W, Fu L, et al. Synthesis and antimicrobial evaluation of 3-methanone-6-substituted-benzofuran derivatives. European Journal of Medicinal Chemistry. 2012;54: 879-86.

3. Tahghighi A, Razmi S, Mahdavi M, Foroumadi P, Ardestani SK, Emami S, et al. Synthesis and anti-leishmanial activity of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines containing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moieties. European Journal of Medicinal Chemistry. 2012 50:124-8.

4. Xiao Z-P, Ouyang H, Wang X-D, Lv P-C, Huang Z-J, Yu S-R, et al. 4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase:Synthesis, molecular docking and antibacterial evaluation. Bioorganic & Medicinal Chemistry. 2011;19: 3884-91.

5. Bondock S, Khalifa W, Fadda AA. Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives

European Journal of Medicinal Chemistry. 2011 46:2555-61.

6. Badr SMI, Barwa RM. Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity. Bioorganic & Medicinal Chemistry. 2011;19 4506-12.

7. Jiang X, Liu W, Zhang W, Jiang F, Gao Z, Zhuang H, et al. Synthesis and antimicrobial evaluation of new benzofuran derivatives. European Journal of Medicinal Chemistry. 2011;46: 3526-30.

8. Abdel-Wahab BF, Abdel-Aziz HA, Ahmed EM. Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1,3-thiazol-2-yl]-1H-pyrazoles. European Journal of Medicinal Chemistry. 2009;44: 2632-5.

9. Abdel-Aziz HA, Mekawey AAI, Dawood KM. Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. European Journal of Medicinal Chemistry. 2009;44: 3637-44.

10. Kirilmis C, Koca M, Servi S, Gur S. Synthesis and Antimicrobial Activity of Dinaphtho[2,1-b]furan-2-yl-methanone and Their Oxime Derivatives. Turk J Chem. 2009;33: 375 - 84.

11. Kalaria R, Odedera RJ, Dave RS, Rajyaguru C, Upadhyay JJ. Synthesis, characterization & antimicrobial activity of substituted tetrahydrothieno[2,3-c]pyridin-2-yl) schiff base derivatives. Journal of Applied Technology in Environmental Sanitation. 2012;2(2):109-14.

12. Iqbal MA, Satyendra D, Apurba T, Patel M, Monika K, Girish K, et al. Synthesis and Antimicrobial screening of some Novel Substituted Thiophenes. Hygeia Journal for Drugs & Medicines. 2012;4(1):112-8.

13. Rajeshwar Y, Naresh K, Jayaveera KN. Synthesis and Antimicrobial Studies of Some Novel Thieno[2,3-d]pyrimidine derivatives. International Journal of PharmTech Research. 2012;4(2):648-54.

14. Hossan ASM, Abu-Melha HMA, Al-Omar MA, Amr AE-GE. Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material. Molecules 2012;17:13642-55.

15. Kheder NA, Mabkhot YN. Synthesis and Antimicrobial Studies of Some Novel Bis-[1,3,4]thiadiazole and Bis-thiazole Pendant to Thieno[2,3-b]thiophene Moiety. International Journal of Molercular Sciences. 2012;13(3):3661–70.

16. Guruprasad BV, Mruthyunayaswamy BHM. Synthesis and antimicrobial activity of some new 3-chloro-6-substituted -N-(substituted 2H-[1,3]oxazino[6,5-b]quinolin-3-(4H,5aH,9aH)-yl)benzo[b]thiopene-2-carboxamides. Indian Journal of Chemistry. 2012;51B:514-20.

17. Aly H, Saleh N, Elhady H. The design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents. Euro J Med Chem. 2011;46:4566-72.

18. Bondock S, Fadaly W, Metwally MA. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. European Journal of Medicinal Chemistry 2010;45:3692-701.

19. Gouda MA, Berghot MA, Abd El-Ghani GE, Khalil AM. The synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. Euro J Med Chem. 2010;45:1338–45.

20. Khalil AM, Berghot MA, Gouda MA. Synthesis and antibacterial activity of some new thiazole and thiophene derivatives. Euro J Med Chem. 2009;44:4434-40.






9


Signature of the candidate :



(BISWAJEET SAHA ROY)


10.


Remarks of the guide:


FORWARDED WITH REQUEST

FOR APPROVAL





11.


Name and designation of:

11.1 GUIDE


11.2 SIGNATURE



Dr. J. SARAVANAN

Prof. and HOD

Department of Pharm Chemistry,

PES College of Pharmacy

Bangalore- 560 050





11.3 CO-GUIDE
11.4 SIGNATURE


NOT APPLICABLE






11.5 HEAD OF THE DEPARTMENT


11.6 SIGNATURE


Dr. J. Saravanan

Prof. and HOD

Department of Pharm Chemistry,

PES College of Pharmacy

Bangalore- 560 050



12.


12.1 REMARKS OF THE PRINCIPAL:


12.2 SIGNATURE: Prof. Dr. S. Mohan

Principal & Director,

PES College of Pharmacy,

Bangalore-560 050




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