International Journal of Research in Pharmacy and Biosciences Volume 5, Issue 2, 2018, PP 8-14 ISSN 2394-5885 (Print) & ISSN 2394-5893 (Online)

Neurology and Psychiatry, and Drugs: S-NICS Investigation

Mina Zakeri1, Majid Monajjemi2* 1Department of Chemistry, Science and research Branch, Islamic Azad University, Tehran, Iran 2Department of Chemical engineering, Central Tehran branch Branch, Islamic Azad University, Tehran, Iran *Corresponding Author: Majid Monajjemi, Department of Chemical engineering, Central Tehran branch Branch, Islamic Azad University, Tehran, Iran.

ABSTRACT There are no works in theoretical of a statistical approach in NMR shielding and nucleus independent chemical shifts for study of antidepressant and antihistamine drugs, while the asymmetry(η)and skew(κ) parameters are fluctuated in small distances and are alternative in large distances in the center of heterocyclic rings for Buclizine, , loratacline, . By changing asymmetry between 0 ≤η≤+1 skew15 will be changed between -1 ≤κ ≤+1 , meanwhile the parameter κ is zero when σ22 = σiso15.In the case of axially-symmetric tensor, σ22 equals15 either σ11 or σ33, skew is κ=±1. In this work, we have investigated the statistical methods by computing of nucleus-independent chemical shifts-SNICS in point of Bq motions in the center of sphere in shielding and de-shielding spaces of antidepressant and antihistamine drugs. In our previous work, it has been exhibited that S-NICS method is an accurate method for estimation the amount of aromaticity in the non-benzene rings such as heterocyclic rings which is a famous for organic chemical compounds as anti-cancer disease. Although NICS values for some molecules such as benzene and naphthalene can be indicated as the aromaticity criterion, for other cases such as antidepressant and antihistamine compounds and their derivatives, S-NICS values are much more accurate compare to NICS index. Keywords: S-NICS, NICS, Buclizine, Cetirizine, loratacline, Promethazine

INTRODUCTION agent is a substance that blocks the neurotransmitter in the central and are drugs which treat allergic the peripheral nervous system. These agents rhinitis and other allergies [1, 2]. Antihistamines inhibit parasympathetic nerve impulses by can give relief when a person has nasal selectively blocking the binding of the congestion, sneezing, or hives because of pollen, neurotransmitter acetylcholine to its receptor in dust mites, or animal allergy. Typically people nerve cells. The nerve fibers of the para take antihistamines as an inexpensive, generic, sympathetic system are responsible for the over-the-counter drug with few side effects. As involuntary movement of smooth muscles an alternative to taking an antihistamine, people present in the gastrointestinal tract, lungs, and who suffer from allergies can instead avoid the many other parts of the body. anti- substance which irritates them [1,2]. Anti are divided into three categories in accordance are usually for short-term treatment. with their specific targets in the central and Chronic allergies increase the risk of health peripheral nervous system: anti-muscarinic- problems which antihistamines might not treat, agents, ganglionic blockers, and neuromuscular including asthma, sinusitis, and lower blockers [3]. respiratory tract infection. Cetirizine, sold under the brand name Zyrtec Buclizine is an antihistamine and anti among others, is a potent second-generation of the diphenyl-methyl- antihistamine used in the treatment of hay fever, group. It is considered to be an , allergies, angioedema, and urticarial. It acts as a similar to [1].In the United Kingdom, selective antagonist of the H1 Buclizine is one of three important drugs for anti receptor. Second-generation antihistamines like depressant and antihistamine. An cetirizine are less able to cross the blood–brain

International Journal of Research in Pharmacy and Biosciences V5 ● I2● 2018 8 Neurology and Psychiatry, Antidepressant and Antihistamine Drugs:S-NICS Investigation barrier and therefore have diminished effects on and contribution. We have shown that the the central nervous system compared to first- asymmetry (η) and skew(κ) parameters fluctuate generation drugs. As such, they are less likely to in behavior around the center of rings due to cause drowsiness or memory impairment [1-4]. minimum isotropy in the center. The most , sold under the brand name Claritin fluctuations are appearing around the minimum among others, is a used to treat or maximum functions mathematically[6]. allergies. This includes allergic rhinitis and Nuclear spin relaxation studies in the gas phase hives. It is also available in combination with had started in 1987. Spin-relaxation data in the pseudoephedrine, a decongestant, known as gas phase provide a stringent test of the loratadine / pseudoephedrine. It is taken by anisotropy of an existing intermolecular mouth [3-5]. Common side effects include potential. The basis of this work is on random sleepiness, dry mouth, and headache. Serious motions of dummy atom in the shielding and de- side effects are rare and include allergic shielding spaces of hetero cyclic rings for reactions, seizures, and liver problems. Use considering maximum abundant of points in due during pregnancy appears to be safe but has not to dipole–dipole, CSA and contribution been well studied [4,5]. It is not recommended relaxations. The main purpose of random in children less than two years old. It is in the displacement of various probes inside of second-generation antihistamine family of shielding and de-shielding spaces are for medication [4,5]. Loratadine was discovered in understanding of mechanism and consequences 1981 and came to market in 1993. It is on the of anisotropic spin–spin interactions in short World Health Organization's List of Essential ranges. Medicines, the most effective and safe In this study, the major components [7-9] of medicines needed in a health system [4-7]. Haeberlen [8] parameterserocyclic rings. The Loratadine is available as a generic medication. numerous random points around the center of Heterocyclic structures played an important role those molecules have been produced by in the metabolism of all cells; large number of generation of pseudo-random numbers, which them are six (or sometimes 5) membered hetero- are distributed in a Gaussian function in the cycles having one to three heteroatoms. interval [0, 1). Recently, antidepressant and antihistamine Our result has been compared by the energy drugs have been attracting much concentration decomposition analysis (EDA) method. The due to its role as attractive scaffolds for total bonding energy and the conjugation biochemical active heterocyclic drugs. Generally, between heteroatoms bonds in heterocyclic chemical-physics and biochemical properties ringsare significantly accurate. like donor-acceptor capability, hydrogen bond, π-π stacking interactions, van der Waals, co- We have optimized the geometries and ordination bonds with metals and in total calculated the carbon NMR for Buclizine, hydrophobic forces have caused the increasing Cetirizine, loratacline, Promethazine molecules interest in anticancer studies for such compounds. for understanding which members of rings are These properties are important of understanding more stable Our methods and physical for their reactivity enable derivatives to readily chemistry approach have been done based on bind with various nucleic acids, anti depressant our previous works [10-110]. and antihistamine drugs and biological structures. RESULTS AND DISCUSSION THEORETICAL BACKGROUND Optimization and NMR shielding constants Aaromaticity in terms of nucleus-independent including orientations of the principal data such chemical shifts in long distances of NICS, as standard components, Haeberlen-Mehring around the ring center, NICS (0), at the center of [8,9] and Herzfeld-Berger[7] parameters for ring plane and aromatic ring current shielding Buclizine, Cetirizine, loratacline, Promethazine (ARCS) were compared in several studies. In compounds in various statistical situations have short range of distances a few works have been been calculated through DFT methods and the done in theoretical and reports the statistical data are listed in tables1,2. The isotropyin all approach in our works [6]. NMR calculations are positive which indicates For further discussion of statistical approach in negative values for aromaticity, but the slopes nucleus independent chemical shift calculations, are decreased from the replacing from 0.1 to especially in short range of distances, it has been center. It is obvious that the difference between focused in relaxations of CAS, dipole-dipole isotropies for NICS data can explain the quality

9 International Journal of Research in Pharmacy and Biosciences V5 ● I2 ● 2018 Neurology and Psychiatry, Antidepressant and Antihistamine Drugs:S-NICS Investigation of the distinct aromaticity for a few molecules, but these differences between isotropies are not able to express the mechanism of aromaticity as well as S-NICS. In the S-NICS method through the statistical calculations, the best point of the shielding space around the center of symmetric or non-symmetric aromatic molecules can evaluated as an aromaticity criterion. And in this method the expectation of the (η*) and (κ*) 16- 18have been estimated as the Gaussian curve functions versus one , two or three dimensional distances around the center of the hetero rings. * The isotropy (σiso ) which is related to all of (η*), (κ *), (Ω*) and ( *) is the best criterion for Figure1. NMR data of Promethazine various aromatic molecules by the S-NICS method, which can express both qualitative and quantitative magnitudes for symmetric or non- symmetric aromatic molecules. Similar to the NICS method, in S-NICS, negative nucleus-independent-chemical-shifts denote aromaticity. There for positive values denote anti-aromaticity. In S-NICS methods, the shielding and de-shielding spaces are significant to discuss the mechanism of the aromatic molecules in point of ring currents, which are the circulating π electrons in an aromatic Figure2. Promethazine optimized via DFT methods molecule produce opposite to the applied magnetic field. The stability of the isotropy criterion is highly affected on the best places in the shielding area spaces and it is dependent on the structures of the aromatic rings. So by using this method, a suitable and stable magnitude of isotropy can calculated as an aromaticity criterion. It is obvious that structural factors cause changes in the magnetic field experienced by the nuclei and change the resonant frequency. Therefore the chemical shielding and many other factors such as electro negativity, hydrogen bonding, and magnetic anisotropy of π-systems will be changed because of the electrons around the Figure3. NMR data of Buclizine proton which produce a magnetic field, countering the applied field. This reduces the field experienced at the nucleus. The electrons are said to shield the proton, an effect that is exactly dependent on the distance of the center. In addition, S-NICS can find the most accurate places for effective points for calculation of isotropy as an aromaticity criterion. The chemical shielding is a vector orientation function for all of the shielding parameters that can change in various places inside the shielding area of the rings for aromatic compounds. Figure4.Optimized of Buclizine

International Journal of Research in Pharmacy and Biosciences V5 ● I2 ● 2018 10 Neurology and Psychiatry, Antidepressant and Antihistamine Drugs:S-NICS Investigation

Figure7. Optimized of cetirizine

Figure5. NMR data of loratacline

Figure6. Optimized of loratacline Figure8. NMR data of cetirizine Table1. S-Nics Value for some atoms of Buclizine and Cetirizine Buclizine, Cetirizine atom charge σiso S-NICS η ∆δ Ω atom charge σiso S-NICS η ∆δ Ω 1 C -0.3372 159.82 165.5 0.7479 16.053 12.245 1 C -0.3380 159.79 162.1 0.7956 16.986 12.613 2 C -0.2952 153.58 151.3 0.1772 39.037 26.024 2 C -0.2959 153.93 154.5 0.2341 -39.65 26.439 3 C -0.0758 143.23 142.4 0.3181 -17.26 17.462 3 C -0.0825 149.74 141.3 0.3712 -26.14 -17.43 4 O -0.2175 148.73 147.6 0.3777 -20.72 13.813 4 C -0.2144 148.93 144.5 0.2412 -23.71 15.809 Cl 0.1568 46.39 48.7 0.7351 -141.8 108.99 5 C 0.1569 46.891 47.5 0.7240 -142.0 109.82 6 N 0.1118 51.21 54.4 0.8325 -124.7 -83.13 6 C 0.1121 50.807 52.5 0.8241 -125.1 -83.46 7 C -0.1392 63.83 64.7 0.8682 128.79 91.858 7 C -0.1507 65.731 66.8 0.8700 -127.8 91.182 Table2. S-Nics Value for some atoms of loratacline, Promethazine loratacline Promethazine atom charge σiso S-NICS η ∆δ Ω atom charge σiso S-NICS η ∆δ Ω 2 C 0.10636 125.821 125.080 0.75498 22.007 16.72 11 C 0.11013 119.165 120.35 0.70343 17.340 13.572 3 C 0.47392 166.57 167.500 0.71481 25.294 19.667 12 C -0.3737 64.053 61.916 0.24449 19.860 21.277 4 O 0.28872 59.477 58.753 0.89718 9.2273 6.1516 16 C 0.37592 63.3365 64.498 0.19539 15.838 17.665 Cl 0.37367 63.685 62.015 0.23134 19.711 21.343 20 C 0.39632 139.00 141.28 0.88827 43.724 29.149 6 N 0.37631 63.32 63. 46 0.19823 15.605 17.364 22 C 0.30669 62.799 65.352 0.88385 14.461 10.235 7 C 0.17426 29.410 28.186 0.83530 10.265 7.457 26 H 0.17646 29.388 28.276 0.82647 10.298 7.517

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Citation: Mina Zakeri & Majid Monajjemi, " Neurology and Psychiatry, Antidepressant and Antihistamine Drugs: S-NICS Investigation ", International Journal of Research in Pharmacy and Biosciences, vol. 5, no. 2, pp. 8-14, 2018.

Copyright: © 2018 Mina Zakeri & Majid Monajjemi. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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