[PDF] Study of Mass Spectra of Some Indole Derivatives

Study of Mass Spectra of Some Indole Derivatives

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American Journal of Analytical Chemistry, 2016, 7, 351-355

Published Online

April 2016 in SciRes. http://www.scirp.org/journal/ajac

How to cite this paper: El Kihel, A., Ahbala, M., Sdassi, H., Ait Sir, H., Mouzdahir, A. and Bauchat, P. (201

6 ) Study of Mass

Spectra of Some Indole Derivatives

. American Journal of Analytical Chemistry, 7, 351-355.

Study of Mass Spectra of Some Indole

Derivatives

A. El Kihel

1* , M. Ahbala 1

H. Sdassi

1 , H. Ait Sir 1 , A. Mouzdahir1 , P. Bauchat 2 1 Laboratoire de Chimie BioOrganique, Faculté des Sciences, El Jadida, Morocco 2

Ciblage et Auto-Assemblages Fonctionnels, UMR 6226, Université de Rennes I, Rennes Cédex, France

Received 7 March 2016; accepted 17 April 2016; published 20 April 2016

Copyright © 201

6 by authors and Scientific Research Publishing Inc.

This work is licensed under the Creative Commons Attribution International License (CC BY).

Abstract

In the work, a study of mass fragmentation routes by the electron-impact mass spectrometry data has been examined for two open chain intermediates of indole derivatives and two pyrroloquino- lines. By the isolation of open chain intermediate and the mass spectra, the structures of pyrrolo- quinoline have been confirmed.

Keywords

Indole, Open-Chain Intermediate, Pyrroloquinoline, Fragments 1.

Introduction

Isolation of open-chain intermediates plays a key role in many synthetic organic reactions. Mass spectra data of

the condensed indoles as pyrroloquinoline and the stability of the intermediates confirm the structure of the pyr-

roloquinolie product.

The indole ring is an important pharmocophore in modern drug discovery. Pyrroloquinoline quinone (PQQ)

presenting the indole moeity, also known as methoxatin, was first identified in methylotrophic bacteria as a

coenzyme for methanol dehydrogenase in 1979 [1]. It is widely distributed in a variety of food and other sources [2]

[3], and is considered to be a redox active nutrient that can produce or scavenge superoxide depending on

different cellular context [4] . In recent years, PQQ has garnered much attention due to its versatile roles in bio-

logical processes, including antioxidant function, cognitive promotion, neuroprotection and cardioprotection [5]-

[7]

. Also, PQQ is reported to have anticancer activity by inducing apoptosis in human Jurkat cells and promo-

nocytic leukemia U937 cells, and this event is associated with generation of reactive oxygen species (ROS)

[4] [8]

Corresponding author.

A. El Kihel et al.

352

This report is concerned with the mass spectra of indole derivatives in order to confirm the structure of the

obtained pyrroloquinolines. 2.

Experimental

MS Measurements

The electron-impact mass spectra were recorded on Varian Mat 311 spectrometer at 70 eV in the Centre de Me-

sures Physiques de l'Ouest (CRMPO) at Rennes 1 University. The electron ionization ion source was kept at

145
. The EI mass spectra were obtained over the range of m/z 10 - 700. 3.

Results and

Discussion

3.1 . Synthesis of the Studied Compounds The studied compounds were synthesized as shown in Scheme 1. Details of the synthetic methods are reported in our articles [9] [10]. Also, all the compounds were previously characterized by mass, 1

H, and

13

C-NMR spec-

tra. Scheme 1 shows the details of the synthetic methods that are reported in our articles [9] [10]. NH NH 2 CH 3 COCH 2 COR , 80°C NH NH NH H 3 C O R N CH 3 R' CH 3 COCH 2 COR

I R=CH

3

II R=OEtIII

R'=CH 3

IV R'=OH

Scheme 1

3.2 . The Open Chain Intermediates I and II The composition of ions determined by exact mass measurements of these compounds are reported in

Scheme 2

and Scheme 3.

In mass spectrometry, the presence of acetyl group is proved by ejection of one methyl radical from the mo-

lecular ion followed by the loss of one molecule of carbon monoxide. The loss of CH 3

CN then HCN fragments

leads to the ions m/z = 116 and 89 for I. This fragment which eliminate one molecule of HCN leading to the ion

m/z = 89 is characteristic in indole fragmentation [11]. The cation m/z = 171 for I was transformed to your tau-

tomer then eliminate a methylene radical leading to the fragment m/z = 157 for I. N H N H H 3 C O CH 3 N H NHH 3 C O m/z = 214 m/z = 199 N H NH CH H 3 C m/z = 171 N H N CH 2 H 3 C -CO N H NH 3 C -CH 2 m/z = 157 N H m/z = 116 -CH 3 CN -HCN m/z = 89 -CH 3 I

Scheme 2

A. El Kihel et al.

353

For the compound II, the presence of the function ester is deduced by splitting of a molecule of ethylene C

2 H 4 following by ejection of one molecule of carbon dioxide giving the fragment m/z = 172. The next fragmentations are similar to those of compound I. N H N H H 3 C O OEt N H NHH 3 C O m/z = 244 m/z = 216 N H NH CH 2 H 3 C m/z = 172 N H N CH 3 H 3 C -CO 2 N H NH 3 C -CH 3 m/z = 157 N H m/z = 116quotesdbs_dbs4.pdfusesText_7