Volume 3, Issue 11, November – 2018 International Journal of Innovative Science and Research Technology

ISSN No:-2456-2165

Methyl Benzyl Amine Substituted Benzopyran-

Biological Activity
Mejo Joseph, Dr Sudhahar .H. Dr S. Alaxander
Nehru College of Pharmacy Vinayaka Mission College of Pharmacy
Pampadi, Kerala Salem, Tamilnadu

Abstract:- Chomene the privileged medicinal

pharmacophore which present as an important structural
component in natural compounds and creatd great
attention because of their pharmacological effect. The
derivatives of chomene moiety can be able of reacting with
avariety of cellular level which leads to their wide ranging
pharmaco- activities such as, anti hepatotoxic, anti B. Quercetin(= 2‐(3, 4‐dihydroxyphenyl)‐3, 5, 7‐trihydroxy‐
inflammatory, diuretic,, antispasmolytic ,estrogenic, 4H‐1‐benzopyran‐4‐one) glycosides and sulfates: chemical
antiviral - helminthic, hypothermal, vasodilatory, anti- synthesis, complexation, and antioxidant properties by B
HIV, antitubercular, herbicidal, anticonvulsant and Alluis, O Dangles - Helvetica ChimicaActa, 2001 - Wiley
analgesic activity. Online Library
I. INTRODUCTION C. Synthesis and evaluation of in vitro antitubercular activity
and antimicrobial activity of some novel 4H-chromeno [2,
Medicinal chemistry is the branch of science, which has 3-d] pyrimidine via 2-amino-4-phenyl-4H-chromene …by
remarkable value for synthesis of novel drugs with intence NR Kamdar, DD Haveliwala, PT Mistry… - Medicinal
therapeutic activity.It concerns with discovery, development, Chemistry …, 2011 – Springer
D. Aryloxyacetic Acid Diuretics with Uricosuric Activity. II.
identification and interpretation of mode of action of
Substituted [(4-Oxo-4H-1-benzopyran-7-yl) oxy] acetic
biologically active compounds at molecular level. These
Acids and the Related Compounds by M Kitagawa, K
developments have provided new challenges and opportunities
for drug research in general and drug design in particular. The YAMAMOTO, S KATAKURA… - Chemical and …,
1991 - jstage.jst.go.jp
major objectives of the medicinal chemists are transformation
of patho biochemical and physiological data into a`chemical E. An efficient synthesis of tetrahydrobenzo [b] pyran
language’ with the aim of designing molecules interacting derivatives using sulfonic acid functionalized silica as an
specifically with the derailed or degenerating processes in the efficient catalyst by GM Ziarani, A Abbasi, A Badiei… -
diseased organisms. Journal of …, 2011 - downloads.hindawi.com

II. ANTIMICROBIAL STUDY

An anti microbal activity was arid out at nehru college of

pharmacy, pampdi, kerala, depratmnt of micro biology lab.
Suitable media prepared with the help of Dr.sudahar D.H.
Details about media,preparation described in methodology
part. F. Tonabersat (SB‐220453) a novel benzopyran with
anticonvulsant properties attenuates trigeminal nerve‐
III. RIVIEW OF LITERATURE induced neurovascular reflexes by AA Parsons, S
Bingham, P Raval… - British journal of …, 2001 - Wiley
A. A Unique Highly Oxygenated Pyrano [4, 3-c][2] Online Library
benzopyran-1, 6-dione Derivative with Antioxidant and G. Synthesis and anticonvulsant activity of 4-oxo and 4-
Cytotoxic Activities from the Fungus Phellinus i gniarius
thioxo-8-bromobenzopyran derivatives by FA Ragab, GS
by Y Wang, SY Mo, SJ Wang, S Li, YC Yang, JG Shi - Hassan, YHA Abu, TA Yahya… - Arzneimittel- …, 2009 -
Organic letters, 2005 - ACS Publications
europepmc.org
H. Identification of (−)-cis-6-acetyl-4S-(3-chloro-4-fluoro-
benzoylamino)-3, 4-dihydro-2, 2-dimethyl-2H-benzo [b]
pyran-3S-ol as a potential antimigraine agent by WN Chan,
JM Evans, MS Hadley, HJ Herdon… - Bioorganic &
medicinal …, 1999 – Elsevier

IJISRT18NV222 www.ijisrt.com 239

Volume 3, Issue 11, November – 2018 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
Vehicle used: Ethanol
IV. SYNTHESIS OF DERIVATIVES
VI. ANTIBACTERIAL SCREENING
To a 50 ml of RBF 250mg (1.066 mmol) of compound 7
was taken in 30ml of ethanol. After that 0.271ml (2.136 mmol, Two Nutrient agar plates were prepared aseptically to get
2 equivalents) of 4-methyl-benzylamine was added reaction a thickness of 5-6 mm. The plates were allowed to solidify and
was refluxed at 800C for 4hours. After completion of reaction inverted to prevent the condensate falling on the agar surface.
the solvent was evaporated. The plates were dried at 370 c before inoculation. The
organisms were inoculated in the plates prepared by spread
M+1 Peak: 313 plate method. i.e, using a micropipette ,the culture place
randomly on the agar plate and it is spread by using L-shaped
glass rod where it is just touch the surface of the agar and
rotating it to to and fro direction.

The organism used were Gram positive S.aureus and Gram

negative Pseudomonas aeroginosa
The standard and test drugs were introduced in two agar plates
by using cup plate method.
 By using the tips of borer, the four agar wells were made at
each quadrant and central well for control.
The anti bacterial screening was carried out in the  Add three different dilution of test drug which has been
pharmaceutical biotechnology laboratory, Nehru College of prepared from previously prepared stock solution of 1g test
Pharmacy ,Pampady,Thrissur. drug per 100mL ethanol.
V. MEDIA USED IN THE STUDY  The different dilutions are prepared by taking 1ML stock
solution and dilute with 4ML solvent(ethanol) similarly
Nutrient agar two more dilutions were prepared in the ratio 2:3 and 3:2.
Nutrient agar at concentration of 2%.(Bacteriological grade)  Also add the standard drug to one well, which has prepared
Ingredients in the ratio 1:4 and ethanol was added as control at the
Peptic digest of animal tissue : 5g/Ltr centre.
Sodium chloride : 5g/Ltr  By kept in the refrigerator for one hour to make uniform
Beef extract : 1.5g/Ltr diffusion of drugs.
Yeast extract : 1.5g/Ltr  Two plates prepared were then incubated for one day..
Agar : 50g/Ltr  The zone of inhibition around the drug and compared with
Final PH( at 250c) : 7.4 of standard. The compound synthesized was tested for
antibacterial activity against gram positive and gram
 Preparation negative bacteria.
The ingredients dissolved in distilled water and heated to
maintain.PH to 7.2-7.6 using alkali diluted acid.15-20ml of Zone of inhibition of the compound against Gram negative
Nutrient Agar was then autoclaved at a pressure of 15psi(120 Pseudomonas aeroginosa
0
c) for 20 min. and the organisms used are S.aureus MTCC Drug used: Test sample(1000mcg/100ml)of different dilution
405,Pseudomonas aeroginosa ,were collected from Institute of in the ratio 1:4, 2:3 & 3:2
Microbial Technology, Chandigarh. The strain was confirmed Standard: Levofloxacin(1mL/4ml)
for their purity and identity by Gram’s staining method and Solvent: Ethanol
characteristic biochemical reactions. The selected strains were
preserved by sub-culturing them periodically on other slants
and storing them under frozen conditions .For the study, fresh
24 hrs broth cultures were used after standardization of the
culture. The entire work was done using horizontal laminar
flow hood at Nehru college. So as to provide aseptic
conditions in absence of bacterial growth. Confirmed by
aseptic working condition. The medium for the experiments
were prepared fresh in Nutrient agar from preserved frozen
slant culture. It as kept incubated at 370 c for one day.
Fig 1
Drug used: t1 (1000mcg/100ml)
Standard used: Levofloxacin (5mcg/disc)

IJISRT18NV222 www.ijisrt.com 240

Volume 3, Issue 11, November – 2018 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
Name of Compounds Dilutions Total Well Zone of Inhibition
organism (compound: Diametre Diametre(W) (T-D)*10
Solvent) (T) (cm) mm
Standrad 1:4 4 0.6 34
Pseudomonas
aeroginosa Solvent _ _ 0.6 _

Sample 1:4 1.5 0.6 8

2:3 1.8 0.6 11
3:2 2 0.6 13
Table 1

Zone of inhibition of the compound against Gram positive

S.aureus
Drug used: Test sample (1000mcg/100ml) of different dilution
in the ratio 1:4, 2:3 & 3:2
Standard: Levofloxacin(1mL/4ml)
Solvent: Ethanol

Fig 2

Name of Compounds Dilutions Total Well Zone of Inhibition

organism (compound : Diametre Diametre (T-D)*10
Solvent) (T) (cm) (W) mm
Standrad 1:4 4.1 0.6 35

Solvent _ _ 0.6 _
S.aureus Sample 1:4 2.3 0.6 16
2:3 2.8 0.6 21
3:2 3.1 0.6 24
Table 2
REFERENCES
VII. RESULT AND DISCUSSION
[1]. Hasan, S. M., et al. "Synthesis of 6-aminomethyl
The antibacterial activity of newly synthesized derivatives of benzopyran-4-one with dual biological
compound was evaluated by using both gram positive and properties: Anti-inflammatory-analgesic and
gram negative organisms..S.aureus, Pseudomonas aeroginosa. antimicrobial." European journal of medicinal chemistry
Various dilution of 1000mcg/100ml has been for the test 44.12 (2009): 4896-4903.
compound, results were compared with the standard [2]. Bonsignore, L., et al. "Synthesis and pharmacological
Levofloxacin 1mL\4mL concentration and ethanol .The results activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide
were interpreted as the KB method The test organism derivatives." European Journal of Medicinal Chemistry
Pseudomonas aeroginosa was found to be moderately 28.6 (1993): 517-520.
sensitive at given concentration of test compound. And the [3]. Wang, Ying, et al. "A Unique Highly Oxygenated
organism S.aureus was found to be highly sensitive at given Pyrano [4, 3-c][2] benzopyran-1, 6-dione Derivative
concentration of test compound. Therefore the drug is more with Antioxidant and Cytotoxic Activities from the
effective against Gram positive organism. Fungus Phellinus i gniarius." Organic letters 7.9 (2005):
1675-1678.

IJISRT18NV222 www.ijisrt.com 241

Volume 3, Issue 11, November – 2018 International Journal of Innovative Science and Research Technology
ISSN No:-2456-2165
[4]. Rajasekaran, S., et al. "Design, synthesis, antibacterial
and in vitro antioxidant activity of substituted 2H-
benzopyran-2-one derivatives." International Journal of
ChemTech Research 3.2 (2011): 555-559.
[5]. Alluis, Bertrand, and Olivier Dangles. "Quercetin (= 2‐
(3, 4‐dihydroxyphenyl)‐3, 5, 7‐trihydroxy‐4H‐1‐
benzopyran‐4‐one) glycosides and sulfates: chemical
synthesis, complexation, and antioxidant properties."
Helvetica ChimicaActa 84.5 (2001): 1133-1156.
[6]. Kamdar, Nimesh R., et al. "Synthesis and evaluation of
in vitro antitubercular activity and antimicrobial activity
of some novel 4H-chromeno [2, 3-d] pyrimidine via 2-
amino-4-phenyl-4H-chromene-3-carbonitriles."
Medicinal Chemistry Research 20.7 (2011): 854-864.
[7]. Kumar, B. Sunil, et al. "An efficient approach towards
three component coupling of one pot reaction for
synthesis of functionalized benzopyrans." Journal of
heterocyclic chemistry 43.6 (2006): 1691-1693.
[8]. Majumdar, K. C., and S. K. Ghosh. "Studies of bioactive
heterocycles: facile thio-Claisen rearrangement of
propargylthio [1] benzopyran-2-ones." Tetrahedron
letters 43.11 (2002): 2115-2117.
[9]. Kitagawa, Masayuki, et al. "Aryloxyacetic Acid
Diuretics with Uricosuric Activity. II. Substituted [(4-
Oxo-4H-1-benzopyran-7-yl) oxy] acetic Acids and the
Related Compounds." Chemical and pharmaceutical
bulletin 39.10 (1991): 2681-2690.
[10]. Ziarani, GhodsiMohammadi, et al. "An efficient
synthesis of tetrahydrobenzo [b] pyran derivatives using
sulfonic acid functionalized silica as an efficient
catalyst." Journal of Chemistry 8.1 (2011): 293-299.

IJISRT18NV222 www.ijisrt.com 242