For Research Work Purpose

1. Ram-Eesh Institute of Vocational & Technical Education, Greater Noida
ISOCHROMAN-4-ONE: PROMISING LEAD IN
RESEARCH
Presenting by:- Snigdha Srivastava
Rajan Kumar Kurmi
Under the guidance of -: Dr. Reema Sinha
Dr .Krishan KumarVerma

2. ABNEGATION
This presentation is made only for
educational purpose only.

3. ABSTRACT
Isochroman-4-one is a polyphenolic natural product , obtain from banana peel.it is widely used as for antihypertensive, antiulceration,
prostrate cancer treatment. This compound is isolated from banana species Musa sapientum L.(peel extract) with strong potency naftopidil
as the lead compound to synthesis and design a novel class of antihypertensive agents bearing arylpiperidine moiety which is identified as
pharmacophore of naftopidil, design for prostatic hypertrophy which acts as a selective alpha-1 blocker or adrenergic receptor antagonist.
Naptopidil had no observable effects on basal heart rate. It is ACE, isomers possess similar pharmacodynamic effects with different
potency R(-) form of isochromanone-4 is more potent than S(+)isochromanone-4 ,it shows similar effect as captopril and reduces systolic
aortic pressure by 16% and diastolic pressure by 18% in animal model but more potent than captopril. It inhibits the activation of post
synaptic alpha-1 receptors by nor-epinephrine thus opposing blood vessel contraction, thus decreases the blood pressure and relieves
symptoms of hypertension, it is an aryl piperazine derivative and piperazine class of drug used in treatment of various diseases like
antianginals, anti-depressant, anti-histaminic, anti-psychotic, urological, anti- helminthic. Mainly they work by the mechanism of alpha-1
adrenergic blockers.
Key words:- Anti-hypertensive, Anti-ulcerative Naftopidil ,Prostrate Hypertrophy,

4. CONTENT
Introduction
Extraction and Isolation
Mechanism
SAR
Synthesis
Future Aspects
References

5. Introduction
 Isochroman-4-one.
 IUPAC-7,8-dihydroxy-3-methyl isochroman-4-one.
 Isolated from banana peel(Musa sapientum L).
 Isolation performed the method of soluble fraction.
1

6.  Compound has shown its potent anti hypertensive activity.
 Isochroman nucleus has produced diverse therapeutically related application in
pharmacological practices.

7. Extraction and Isolation
Cut banana peel into small pieces
Extract with 95% ethanol(Ratio is 1:6 w/v)
Soaked for 24hrs
Brown gum Obtained

8. Suspend in Distilled water
Extracted with petroleum ether (8 times)
Again extracted with ethyl acetate(8 times)
Concentrated above collected extract kept in vacuo
Wash the compound with epoxy pseudo iso eugenol-2-methyl
(EPE).

9. Shows Pharmacological activity in the renal hypertension.
By working as ACE inhibitor.
Currently reported as moderate antihypertensive activity.
Additional activity has been reported on α1-adrenergic receptor.
 Exhibit strongest inhibitory activity of β1 adrenergic blocking activity.
Inhibition ratio – 44.7% (systolic & diastolic pressure).
Mechanism

10. R1
Naftopidil
(A)
(B)
Resultant compound

11. SAR
Analysis of SAR revealed, substituted position of linked given impact on vasodilation potency.
C-6 position substitution show more potent activity than C-7 & C-8 substitution.
Here this structure of isochroman derivative responsive on Systolic and Diastolic Hypertension
Substitution at piperazine moiety, furan is not showing desired activity.
Also on benzene ring substitution infleuences increased the vasodilation potency.
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2
3
4
5
8
6
7
9
10
Isochroman derivative

12. Synthesis
Lab synthesis :-
R1=R2=R3=R4= Me,H

13. Uses-: Anti-hypertensive , Anti-inflammatory, Anti-oxidant

14. Future Aspects
Isochroman-4-one may be Lead molecules for:-
Anti histaminic agent (H1)
Anti parasitic agent
Helpful in Covid-19 Treatment

15. References
G. Albano, L.A. Aronica, “Potentiality and synthesis of O- and N-heterocycle: Pd-catalyzed
cyclocarbonylative sonogashira coupling as a valuable route to phthalans, isochromans, and
isoindolines”,Eur. J. Org Chem. (2017) 7204e7221.
M. El Riachy, F. “Priego-Capote, L. Leon, L. Rallo, M. Dolores Luque de Castro, Hydrophilic
antioxidants of virgin olive oil. Part 1: hydrophilic phenols: a key factor for virgin olive oil
quality”, Eur. J. Lipid Sci. Technol. 113 (2011) 678e691.
A. Wang, Y. Xu, Y. Gao, Q. Huang, X. Luo, H. An, J. Dong, “Chemical and bioactive diversities of the
genera Stachybotrys and Memnoniella secondary metabolites, Phytochemistry”, Rev. 14 (2015)
623e655.
A. Saeed, “Isocoumarins, miraculous natural products blessed with diverse pharmacological
activities”, Eur. J. Med. Chem. 116 (2016) 290e317.