International Journal of Current Research and Review
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IJCRR - Vol 03 Issue 04, April, 2011

Pages: 53-68

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SYNTHESIS, SPECTRAL ANALYSIS AND BIOLOGICAL STUDIES ON 6-METHYL-7, 9-
DIPHENYL-1, 4, 8-TRIAZASPIRO [4.5] DECANE

Author: N.Manivannan, B.Elanchezhian, G.Selvanathan, K.Pandiarajan

Category: General Sciences

Abstract:The title of the molecule 6-methyl-7, 9-diphenyl-1, 4, 8-triazaspiro (4.5) decane is synthesized from the condensation reaction of ethylenediamine with (t)3-methyl-r(2),c(6)-diphenyl Piperidin- 4-one. The product is evidenced by IR, 1H NMR and 13C NMR spectra. In the 1H NMR study, it is found that the ABX spin system belongs to this molecule.The second-order analysis based on the method developed by Bernstein etal is used for ABX system.The parameters of coupling constants (3J9a, 10a = 11.46 Hz and 3J9a, 10e =2.46Hz) and origin of chemical shifts (υA=1.77 and υB=1.86ppm) are calculated using ABX system from which also found that the title molecule adopt chair conformation. These results also confirm that the substitutions of Phenyl and methyl groups are in equatorial position of the six memberd piperidine ring of the title compound. The Biological (antibacterial and antifungal) activities of title compound have also been studied.

Keywords: Ethylenediamine, triazaspiro decane, Spiro, ABX, second-order, conformation, antibacterial, antifungal.

Full Text:

INTRODUCTION

The 6-methyl-7, 9-diphenyl-1, 4, 8- triazaspiro (4.5) decane is a ABX spin systems which have attracted considerable interest from the chemistry community as they represent promising building blocks with potential applications in the field of pharmaceuticals.Artificial product synthesis also diverse key synthetic catalyst. The 6- methyl-7, 9-diphenyl-1, 4, 8-triazaspiro (4.5) decane can be consist of symmetrical substitutions of phenyl with piperidine ring as diphenyl piperidine extended with methyl group. A linear fused or bridged systems, spirocyclic core systems are less common in known drugs and natural products. Some examples of spirocyclic natural product contain ring nitrogen include cephalotaxine, halichlorine, histrionicotoxin, triazaspiro and manzamine. In the area of nonnatural compounds spirocyclic nitrogen-containing systems are fashioned into compounds displaying interesting biological activities. Such spiro scaffolds can be classified according to the ring size of the heterocyclic ring. The interplay of the structural variation is resulted in compound ranging from the inactive to the extraordinary potent belongs to the above statement.We expect that, fusing imidazolidine ring and piperidine ring cause new biological activity. NMR spectral studies of heterocyclic compounds have helped in understanding the influence of electronic and conformational effects on chemical shifts and coupling constants .The conformational studies of heterocyclic compounds also have been made using NMR spectra [1-2]. Several NMR spectral studies [3-5], have been reported on 2,6- diaryl piperidine derivatives. The reaction of 1,2 diamines with carbonyl compounds provide Imidazolidines. The imidazolidine is the guiding principle of bond formation occurring via reaction of a binucleophillic component with an electron-deficient bielectrophilic counter.The five membered heterocyclic belong with two heteroatom at 1 and 3 position from the reaction of a 1,4- binucleophile with a 1,1-bielectrophile [6- 11]. Generally, 1,4 binucleophiles are encountered Ethylenediamine , Ethylene glycol and 1,1- Bielectrophile. Many of the common reagents are used as RCOR, RCHO, Carboxylic chlorides and phosgene. In the absence of reagent, the five membered rings are coupled by one carbon unit with piperidine ring. Because of this coupling, the piperidine ring is gained antifungal and antibacterial activities.

2. Experimental Methods

The reactant materials such as ammonium acetate, ethylmethylketone, benzaldehyde, benzene, potassium carbonate and petroleum-ether (60-80º C) are purchased from Sigma Aldrich chemicals, U.S.A. which is of spectroscopic grade is used for recording the spectra as such without any further purification. The product 6-methyl- 7,9-diphenyl-1,4,8-triazaspiro (4.5) decane is prepared by a Stirred solution of(AR)Ethylenediamine (15 mmol) in (AR) Benzene (45 ml), t(3)- methyl r(2) and c(6)- diphenylpiperidin-4-one (15 mmol). The reaction flask is fitted with a Dean - stark water separator.Which is charged with anhydrous K2CO3 and the solution is gently refluxed for 14 hrs and cooled room temperature [12-14]. The yellow oily solution is obtained and then (AR) petroleum ether (60-80 ºc) was added. The product is separated as pale yellow solid. It is recrystallized from Benzene, petroleum - ether. After recrystallization the melting point is observed at 71-72 ºC. (Yield -90%). The reaction scheme of the title molecule is given in figure 1

The FT-IR spectrum of the compound is recorded in Bruker IFS 66V spectrometer in the range of 4000-100cm-1 . The 1HNMR spectral analysis is carried out using Bruker AMX-400 NMR spectrometer operating at frequency 400 MHZ using deutriated chloroform .The 13CNMR spectral analysis is also carried out using Bruker AMX- 400 NMR spectrometer operating at frequency 100 MHZ.

2.1. Biological Activities:

About 0.03g of compound 6-methyl-7,9- diphenyl-1,4,8-triazaspiro(4.5) decane is dissolved in a suitable solvent such as (AR) ethanol, (AR) petroleum ether etc Muller Hinton Agar medium (MHA) – Antibacterial. Seaboard Dextrose Agar medium (SDA) Antifungal is Carried out Agar diffusion method.

3. Results and Discussion

Ethylenediamine is condensed [15] with t(3)-methyl-2,6-diphenylpiperidin-4-one and the product is carried out by scheme-1.The product was identified as 6-methyl -7,9- diphyl-1,4,8-triazaspiro (4.5) decane by IR, 1H and 13C NMR spectral studies. The structure of compound–II (6-methyl-7,9- diphyl-1,4,8-triazaspiro(4.5)decane) is shown in Figure 2.

The IR spectrum of compound (I) shown in Figure 3, a strong band at 1701 cm-1 is observed. But in the compound (II) that the carbonyl group weak band at 1701 cm-1 is observed . IR spectrum of compound (II) is shown in Figure 4. 3273 cm-1 (NH, str), 3060 cm-1 (Aromatic CH stretching), 2967(Aliphatic CH stretching), 1437 and 1375 cm-1 (Antisymmetric deformation of CH in C- CH3), 1113cm-1 (C- N stretching), 702cm-1 C6 H5 – ring deformation). 1H NMR spectral data‘s of title compound (II)is presented in the table 1and2 and the corresponding spectrum is given in figure 5and6.H9a – δ4.10 (H,dd), H7a - δ 3.70 (1H.d), H10a - δ 1.75 (1H,t), H10e – δ 1.89(H, dd) H6a- δ 2.04 (H ,m), CH3 - δ 0.64 (3H,d),C2 and C3 (CH2 )- δ 3.11 - δ 2.85 (4H.m), Aromatic- δ 7.15 - δ 7.55 (10H, m), N-H- δ 1.63 (3H- broad Singlet). 13C NMR spectral data‘s of title compound (II) is given in table-3 and the corresponding figure is presented in the figure 7. C5 - δ 80.28, C7 - δ 66.12, C9- δ 59.10, C2- δ 45.80,C3- δ 46.0, C6- δ 46.5, C10- δ 47.85, CH3- δ 10.48, aromatic ipso δ 144.7, δ 143.7, ortho- δ 126.9, δ 128.1, meta- δ 128.38, δ 128.32, Para- δ 127.1, δ 127.4.ppm.

AMX Calculation:

The spacing between centre of the signals are 10a and 10e is 40 HZ. The coupling constant between them is obtained from the signal 10e as 12Hz. The value ?υ/J is much less than 6 Hence protons H9a, 10a and 10e from an ABX system [16-18]. The coupling constant JAB and the chemical shift of proton X can be directly calculated from the observed spectral data. The actual value of JAX will be higher than that form the spectrum. The real value of JBX will be less than that obtained from the spectrum. Let υA and υB are actual chemical shifts of proton A and B in Hz. Let υ'A and υ'B centers of the observed signal from protons A and B actual value of JAx and JBx are calculated as follows.

3.1. Conformation of the piperidine ring in Compound - II

The coupling constant are 3 J9a, 10a is 11.46 and 3 J6a, 7a is 10.3 Hz. The coupling constant 3 J9a, 10e is 2.46 HZ. These values are indicated that the piperidine ring in the title of compound adopts a chair conformation [19] as shown in Figure 8and 8(A, BandC)

 

It is of interest to compare the 1HNMR spectral data of compound-II with those of 6-methyl-7,9-diphenyl-8-aza-4-oxa-1-thio Spiro[4.5]decane [20] (III) and 3-methylr(2),c(6)-diphenylpiperidine(IV) [21-23].For such comparison the 1H NMR spectral data of II,III and IV are given in Table-4 and 13C NMR spectral data of II,III and IV are given in Table-5.

II- 6-methyl-7,9-diphyl-1,4,8- triazaspiro(4.5)decane. III- 6-methyl-7,9-diphenyl-8-aza-4-oxa-1- thio Spiro[4.5]decane. IV- 3-methyl-r(2),c(6)-diphenylpiperidine. 1H NMR chemical shifts (ppm) of Compound II, III and IV Protons H7a and H9a are shifted to high frequency by 0.30 and 0.46 ppm in II than in IV. This is due to proximity interaction between the axial Nitrogen at C-5 and axial Hydrogen‘s H7a and H9a. A similar shift is observed in III .The methylene protons at C- 2 and C-3 appear at 2.85 -3.11 ppm as a complex pattern in II. In III protons at C-2 appear at 2.99 ppm those at C-3 appear at 4.06 ppm. This is due to a grater electro negativity of oxygen than Nitrogen. Benzylic carbons at C-7 and C-9 are shifted to lower frequency by 4.08 and 3.60 ppm in II than in IV this is due to the proximity interaction of the axial Nitrogen at C-5, which polarizes the C-H bonds at C-7 and C-9. A partial positive charge is accumulated on protons, which shifts the protons signal to higher frequency. A partial negative charge is accumulated on carbon, which shifts the carbon signal to lower frequency.

3C NMR chemical shifts (ppm) of Compound II, III and IV Benzylic carbons at C-7 and C-9 are shifted to lower frequency by 4.08 and 3.60 ppm in II than in IV this is due to the proximity interaction of the axial Nitrogen at C-5, which polarizes the C-H bonds at C-7 and C-9. A partial positive charge is accumulated on protons, which shifts the protons signal to higher frequency. A partial negative charge is acumulated on carbon, which shifts the carbon signal to lower frequency.

3.2. Biological activities of the compound

The compound 6-methyl-7,9-diphenyl- 1,4,8-triazaspiro[4.5]decane is treated with selected bacterial [24] and fungal [25] organisms. The bacterial organisms are used in E.coli, Pseudomonas, aeruginnosa, bacillus cereus, salmonella spp and klebsiella pneumonia. The fungal organisms are used in alternaria spp, Fusarium Spp, Aspergillus Niger, Aspergillus flavus and penicillium notatum. MR. methyl red, VP-vogues proskauer,TSI – Triple sugar iron, GNB – Gram negative Bacilli,GPB – Gram positive bacilli, A/A – Acid slant bacilli, K/K- Alkaline salt alkaline bacilli ,K/Aalkaline salt Acid bacilli] .A-Acid, (+ ) positive, (-) – Negative. The results of biological characteristics of bacterial-organism and antibacterial activity are presented in table 6 and 7 respectively and their photos are given in figure 9(9a,9b,9c,9d and 9d). The antifungal activity of title molecule is presented in table 8 and it‘s photos are given in figure 10(10a,10b,10c,10d and10e).

4. CONCLUSION

The 6-methyl-7, 9-diphenyl-1, 4, 8- triazaspiro (4.5) decane is synthesized from the condensation reaction of ethylenediamine with (t) 3-methyl- r (2), c (6) - diphenyl Piperidin-4-one. The IR, 1HNMR and 13C NMR spectral analyses have been carried out. The title compound is investigated for antibacterial and antifungal activities using MHA and SDA medium. The organisms like E. coli, pseudomonas aeruginnosa, salmonella spp klebsiella pneumonia and bacillus cereus for antibacterial and alternation spp, Fusarium spp, asparagus Niger, Aspergillums flavus, and penicillium notatum for antifungal. From the analyses it is found that the compound has good antibacterial and antifungal microbial activities. The vicinal coupling constants suggest that the piperidine ring of the compound has chair conformation. The methyl group at C-6 and two phenyl groups at C -7, C- 9 are equatorially oriented. Because of the wide pharmaceutical application, this compound can be used for the manufacturing the drugs.

ACKNOWLEDGEMENTS

Authors of this article are thankful to the Dr. K. Pandiarajan, Dept of chemistry, Annamalai University, Chidambaram, V.Stalinelanchezhian research scholar, Madras University, Bhuvaneswari Department of microbiology, A.V.C.College (Autonomous), for their constant encouragement, necessary facilities and Indian Institute of Science Bangalore for spectral data's.

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A study by Amruta Choudhary et al. entitled "Family Planning Knowledge, Attitude and Practice Among Women of Reproductive Age from Rural Area of Central India" is awarded Best Article for special issue "Modern Therapeutics Applications"
A study by Raunak Das entitled "Study of Cardiovascular Dysfunctions in Interstitial Lung Diseas epatients by Correlating the Levels of Serum NT PRO BNP and Microalbuminuria (Biomarkers of Cardiovascular Dysfunction) with Echocardiographic, Bronchoscopic and HighResolution Computed Tomography Findings of These ILD Patients" is awarded Best Article of Vol 12 issue 13 
A Study by Kannamani Ramasamy et al. entitled "COVID-19 Situation at Chennai City – Forecasting for the Better Pandemic Management" is awarded best article for  Vol 12 issue 12
A Study by Muhammet Lutfi SELCUK and Fatma entitled "Distinction of Gray and White Matter for Some Histological Staining Methods in New Zealand Rabbit's Brain" is awarded best article for  Vol 12 issue 11
A Study by Anamul Haq et al. entitled "Etiology of Abnormal Uterine Bleeding in Adolescents – Emphasis Upon Polycystic Ovarian Syndrome" is awarded best article for  Vol 12 issue 10
A Study by entitled "Estimation of Reference Interval of Serum Progesterone During Three Trimesters of Normal Pregnancy in a Tertiary Care Hospital of Kolkata" is awarded best article for  Vol 12 issue 09
A Study by Ilona Gracie De Souza & Pavan Kumar G. entitled "Effect of Releasing Myofascial Chain in Patients with Patellofemoral Pain Syndrome - A Randomized Clinical Trial" is awarded best article for  Vol 12 issue 08
A Study by Virendra Atam et. al. entitled "Clinical Profile and Short - Term Mortality Predictors in Acute Stroke with Emphasis on Stress Hyperglycemia and THRIVE Score : An Observational Study" is awarded best article for  Vol 12 issue 07
A Study by K. Krupashree et. al. entitled "Protective Effects of Picrorhizakurroa Against Fumonisin B1 Induced Hepatotoxicity in Mice" is awarded best article for issue Vol 10 issue 20
A study by Mithun K.P. et al "Larvicidal Activity of Crude Solanum Nigrum Leaf and Berries Extract Against Dengue Vector-Aedesaegypti" is awarded Best Article for Vol 10 issue 14 of IJCRR
A study by Asha Menon "Women in Child Care and Early Education: Truly Nontraditional Work" is awarded Best Article for Vol 10 issue 13
A study by Deep J. M. "Prevalence of Molar-Incisor Hypomineralization in 7-13 Years Old Children of Biratnagar, Nepal: A Cross Sectional Study" is awarded Best Article for Vol 10 issue 11 of IJCRR
A review by Chitra et al to analyse relation between Obesity and Type 2 diabetes is awarded 'Best Article' for Vol 10 issue 10 by IJCRR. 
A study by Karanpreet et al "Pregnancy Induced Hypertension: A Study on Its Multisystem Involvement" is given Best Paper Award for Vol 10 issue 09

List of Awardees

A Study by Ese Anibor et al. "Evaluation of Temporomandibular Joint Disorders Among Delta State University Students in Abraka, Nigeria" from Vol 13 issue 16 received Emerging Researcher Award


A Study by Alkhansa Mahmoud et al. entitled "mRNA Expression of Somatostatin Receptors (1-5) in MCF7 and MDA-MB231 Breast Cancer Cells" from Vol 13 issue 06 received Emerging Researcher Award


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International Journal of Current Research and Review (IJCRR) provides platform for researchers to publish and discuss their original research and review work. IJCRR can not be held responsible for views, opinions and written statements of researchers published in this journal

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