Biological Sciences
Azole
Azoles are a class of organic compounds that contain a five-membered ring with at least one nitrogen atom. They are widely used as antifungal agents in medicine and agriculture due to their ability to inhibit the synthesis of ergosterol, an essential component of fungal cell membranes. Azoles are also used in the synthesis of various pharmaceuticals and agrochemicals.
Written by Perlego with AI-assistance
Related key terms
1 of 5
3 Key excerpts on "Azole"
- Charles H. Nightingale, Paul G. Ambrose, George L. Drusano, Takeo Murakawa, Charles H. Nightingale, Paul G. Ambrose, George L. Drusano, Takeo Murakawa(Authors)
- 2007(Publication Date)
- CRC Press(Publisher)
Where applicable, differences for filamentous fungi will be highlighted. The primary goal of this chapter is to give an overview of exposure – response relationships of Azoles in vitro and in vivo. After a brief description and overview of the class, the pharmacokinetics of the major Azoles is portrayed in order to discuss the exposure of the drug in human. Next, concentration – effect relationships are described, and finally the exposure – response relationship in vivo, both in animals and in men. BRIEF HISTORY OF THE CLASS During the Second World War, in the wake of the discovery of penicillin in the previous decade and the development to its clinical use, a quest for other drugs with activity against infectious agents led to the discovery in 1944 that benzimida-zole possessed, apart from antibacterial, antimycotic activity (4). The activity was attributed initially to competitive inhibition between this drug and the purines adenine and guanine, but the mechanism of action later described proved to be inhibition of ergosterol synthesis through the cytochrome P-450 system (see 327 below). In 1952, Jerchel (5) described several analogs that had profoundly increased antimicrobial activity. During the next decades, a large number of antifungals from this class were studied extensively to determine possible clinical use. The first Azole to be used clinically was chlormidAzole, used as a topical agent. Other compounds, still in use today, include clotrimAzole and econAzole but can be used as topical agents only. In general, imidAzoles could not be used systemically, mainly because of hepatotoxicity and major drug interaction effects. A major area of application is hair, skin, and nail infections, because topical use is a good alternative in most cases. The only noticeable exceptions were miconAzole (6) and, later, ketoconAzole (7).
eBook - PDFChemical and Biochemical Engineering
New Materials and Developed Components
- Ali Pourhashemi, Gennady E. Zaikov, A. K. Haghi, Ali Pourhashemi, Gennady E. Zaikov, A. K. Haghi(Authors)
- 2015(Publication Date)
- Apple Academic Press(Publisher)
5.1 INTRODUCTION The heterocyclic compounds have received special attention as they be-long to a class of compounds with proven physiological action. There are numerous biologically active molecules with five membered rings, con-taining two hetero atoms. ThiAzole is an important scaffold known to be associated with several biological activities. The occurrence of thiAzole ring system in numerous biologically active molecules has been recognized which plays an important role in animal and plant kingdom. Different thiAzole bearing compounds possess activi-ties such as antibacterial [35], antifungal [39], anti�infla ��atory [19], an -tihypertensive [32], anti�HIV [3], antitu�or [26], anti filarial [27] anticon -vulsant [29], herbicidal, insecticidal, schistosomicidal and anthelmintic [30]. The presence of thiAzole ring in vitamin B 1 and its coenzyme play an important role as electron sink and for the decarboxylation of α -keto acids, respectively [8]. Many biologically active products, such as Bleo-mycin and Tiazofurin (antineoplastic agents) [31], Ritonavir (anti-HIV drug) [12], Fanetizole ( N -phenethyl-4-phenylthiazol-2-amine), Fentiazac [(2-(4-(4-chlorophenyl)-2-phenylthiazol-5-yl)acetic acid)], Fenclozic acid ([2-(4-chlorophenyl)-1,3-thiazol-4-yl] acetic acid] and Meloxicam (anti�infla ��atory agents) [28], RavuconAzole (4�(2�((2 R ,3 R )-3-(2,4-difluorophenyl)�3�hydro �yl �4�(1 H -1,2,4-triazol-1-yl)butan-2-yl)thiazol-4-yl)benzonitrile) and Abafungin (antifungal agents), Nizatidine (antiul-cer agent) [24], imidacloprid (insecticide) and penicillin (antibiotic) are ThiAzole: A Simple Scaffold with Tremendous Therapeutic Potential 45 some examples of thiAzole bearing products. ThiAzole derivatives are also widely used for the synthesis of antibiotic sulphathiAzole [7], and with poly oxygenated phenyl component they showed promising antifungal ac-tivity.
eBook - ePubN-Sulfonated-N-Heterocycles
Synthesis, Chemistry, and Biological Applications
- Galal H. Elgemeie, Rasha A. Azzam, Wafaa A. Zaghary, Ashraf A. Aly, Nadia H Metwally, Mona O. Sarhan, Elshimaa M. Abdelhafez, Rasha E. Elsayed(Authors)
- 2022(Publication Date)
- Elsevier(Publisher)
Chapter 4N -Sulfonated N -Azoles: Synthesis, chemistry and biological applications
Abstract
The N -tosyl moiety is a robust constituent of numerous pharmaceutical molecules. It has drawn enormous attention to exploring the efficient hybridization of N -tosyl moiety with nitrogen-containing five-membered heterocyclic rings. In this chapter, we focus on N -sulfonated five-membered rings which include five important classes named N -sulfonated-pyrrole, -isoxAzole, -oxAzole, -isothiAzole, and –thiAzole derivatives. Furthermore, recent reported synthetic methodologies are focused on their synthesis as well as their intriguing biological properties. For example, N -tosyl pyrrole derivatives demonstrated anticancer and antiviral activities.Keywords
N -sulfonated pyrroles; N -sulfonated isoxAzoles; N -sulfonated oxAzoles; N -sulfonated isothiAzoles; N -sulfonated thiAzoles; heterocyclic synthesis; biological activity4.1 Introduction
Natural products that contain functional groups with heteroatom-heteroatom linkages (X–X, where X=N, O, S, and P) are a small yet intriguing group of metabolites. Functional groups containing X–X bonds are found in all major classes of natural products and often impart significant biological activity [1] . Pyrroles are ubiquitous structural motifs in pharmaceutical agents and smart materials [2] . OxAzoles have been elucidated as potential antibacterial, antifungal, anticancer, antiviral, and antioxidation agents, monoamine oxidase inhibitors, etc . Indolyl-oxAzole derivatives [3 –5] are an important class of oxAzole-type natural products, and these natural compounds and their derivatives have been demonstrated to exhibit broad biological and pharmaceutical activities. ThiAzole is a good pharmacophore nucleus due to its various pharmaceutical applications. Its derivatives have a wide range of biological activities, such as antioxidant, analgesic, and antimicrobial, including antibacterial, antifungal, antimalarial, anticancer, antiallergic, antihypertensive, antiinflammatory, and antipsychotic activities [6] . From the point of view that sulfonated drug metabolites may be pharmacologically more active than their respective parent drugs, the synthesis of N -sulfonated heterocycles would be of interest in the field of synthetic new drugs [7 ,8] . In this chapter, we focus our attention on only one N -sulfonated five-membered ring, which includes five important classes named N
Index pages curate the most relevant extracts from our library of academic textbooks. They’ve been created using an in-house natural language model (NLM), each adding context and meaning to key research topics.
