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Penicillin, Cephalosporin, and Streptomycin Production
Published in Debabrata Das, Soumya Pandit, Industrial Biotechnology, 2021
The composition of beta-lactam is not very typical and apart from the antibiotic classes to be listed, it is present only in certain alkaloids and some anti-metabolite toxins, including pachystermines from Pachystradra terminals (Chang et al., 2000), Pseudomonas tabici producing wild-fire poison (Yi et al., 1990) and even Streptomyces verticillus producing anti-tumour antibiotics, phleomycins and bleomycin (Kawano et al., 2000). The commonly used beta-lactam antibiotics are penicillins and cephalosporins whereas some fairly recent members are cephamycins, nocardicins, thienamycins. Apart from nocardicins, the above antibiotics are derivatives of bicyclic core structures wherein the lactam ring unifies with the ring molecule employing a nitrogen atom and a carbon atom (Figure 12.2). This ring compound is 5-membered in penicillins (thiazolidine), thienamycins (pyrroline), and clavulanic acid (oxazolidine). It is 6-membered in cephalosporins and cephamycins (dihydro-thiazolidine). Beta-lactam antibiotics prevent the development of the bacterial cell membrane's peptidoglycan. Given the absence of this factor in mammalian cells, beta-lactam antibiotics have low toxicity to mammals (Bruggink et al., 1998).
Polypeptides
Published in Stanislaw Penczek, H. R. Kricheldorf, A. Le Borgne, N. Spassky, T. Uryu, P. Klosinski, Models of Biopolymers by Ring-Opening Polymerization, 2018
However, it is noteworthy that symmetric cyclic anhydrides, such as succinic anhydride, exhibit a similar pattern of "carbonyl bands". In this case, the so-called "Fermi coupling" of the two originally identical CO frequencies is considered to explain the existence of two carbonyl bands of different extinction coefficients.66 Nonetheless, there is an experimental evidence that the assignment of the vibration at 1785 cm-1 to the carbamoyl group is correct, namely a comparison with thiazolidine-2,5-diones and 2-thioxo-oxazolidine-5-ones (Formula 32b, c).25,67,68 The latter class of cyclic anhydrides only exhibits the carbonyl band around 1850 cm-1.15,68
Production of Antibiotics and Anti-Tumor Agents
Published in Nduka Okafor, Benedict C. Okeke, Modern Industrial Microbiology and Biotechnology, 2017
Nduka Okafor, Benedict C. Okeke
The Beta-lactam antibiotics include the well-established and clinically important penicillins and cephalosphorins as well as some relatively newer members: cephamycins, nocardicins, thienamycins, and clavulanic acid. Except in the case of nocardicins, these antibiotics are derivatives of bicyclic ring systems in which the lactam ring is fused through a nitrogen atom and a carbon atom to ring compound. This ring compound is five-membered in penicillins (thiazolidine), thienamycins (pyrroline) and clavulanic acid (oxazolidine); it is six-membered (dihydrothiazolidine) in cephalosporins and cephamycins (Fig. 25.1).
Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one
Published in Journal of Sulfur Chemistry, 2021
T. Bensafi, D. Hadji, A. Yahiaoui, K. Argoub, A. Hachemaoui, A. Kenane, B. Baroudi, K. Toubal, A. Djafri, A. M. Benkouider
Thiazolidinone and its derivatives are leading scaffolds in heterocyclic chemistry due to the demonstration of their broad spectrum of activity, which they present in very varied fields. The 2-thioxo-1,3-thiazolidin-4-ones (2-thioxo-4-thiazolidinones/2-thio-2,4-thiazolidinediones) commonly known as rhodanine one of 4-thiazolidinones subtypes derived from thiazolidine are five-membered heterocyclic compounds, which have a sulfur atom at their 1-position, a thiocarbonyl group at their 2-position, a nitrogen atom at their 3-position, and a carbonyl group at their 4-position. It is substantially similar in structure with thiazolidine-2,4-dione and 2-iminothiazolidine-4-one that include an oxo or imino group, respectively, instead of the thioxo group at position 2. Also, with 4-thioxothiazolidin-2-one, which bears oxo and thioxo groups at positions opposite to those in rhodanine. These analogs differ in their biological activities [1]. The rhodanine structure is not prevalent in nature. Literature reports numerous routes for the preparation of rhodanine moieties [2,3] such as the reaction of ammonia or primary amines with carbon disulfide and chloroacetic acid in the presence of bases or the addition of isothiocyanate to mercaptoacetic acid followed by acid-catalyzed cyclization [4,5]. Over the last 15 years, rhodanine derivatives have gained much attention due to their outstanding biological activities and have undergone rapid development as antidiabetic [6,7] antifungal [8], antimalarial [9], antiproliferative [10], antihepatitis C virus (HCV) [11], anticancer [12], antimicrobial [13], anti-apoptotic [14], and antibacterial [15]. These compounds are extensively used as anti-HIV and potent anti-HSV microbicides [16,17]. Besides, the use of other rhodanine-based molecules as an inhibitor of UDP-N-acetylmuramate/L-alanine ligase [18], oncolytic phosphatase (PRL-3) [19], JNK-stimulatory phosphatase-1 (JSP-1) [20], cholphosphate mannose synthase [21], tyrosinase [22], β-lactamase [23], 15-lipoxygenase [24], Mur ligase [25], and histidine decarboxylase [26] has also been reported. For several years, great effort has been devoted to the study of five-membered rings with nitrogen, sulfur, and oxygen atoms as active centers; they are effective inhibitors for the corrosion of metals [27–32].
Condensation–cyclization reaction for one-pot synthesis of 1,3-thiazolidin-4-one derivatives by poly(p-phenylenediamine) grafted on LDHs as a catalyst with green tool
Published in Journal of Sulfur Chemistry, 2021
Maryam Mirzaei-Mosbat, Ramin Ghorbani-Vaghei
Thiazolidine-4-one is a five-membered heterocyclic ring with N and S heteroatoms and one carbonyl group, utilized in many strategies for fabrication of the pharmaceuticals, and therefore, it is present in the structure of the fabricated medicines [10–13]. Nowadays, innumerable studies have been carried out around the world to investigate the biological activity of thiazolidine-4-one, whose extensive applications have been demonstrated in a variety of domains, e.g. anti-HIV [14–18], antimicrobials [19,20], antihistamines [21,22], anti-YFV (Yellow fever virus) [23], anti-cancers [24], anti-inflammatories [25], and antioxidants [26]. It is noticeable that the fabrication of assorted derivatives with various biological properties can be carried out by modification of the substitutions which exist in the structure of the compounds. For example, Rawal et al. could introduce a type of derivatives named 2,3-diaryl-1,3-thiazolidin-4-one, which is a vital drug for the therapy of the HIV virus [16]. Regarding the above-mentioned importance and applications of thiazolidinones in pharmaceutical industry and commercial markets, finding the superior synthesis approaches is very important. So far, innumerable approaches have been proposed by researchers for the fabrication of thiazolidinediones, among which there is a commonly employed strategy which consists of one-pot three-component condensation of amine, the carbonyl compound and thioglycolic acid. According to the literatures, various conditions and catalysts have been investigated in this reaction. For instance, in 2002, Srivastava et al. [27] synthesized 4-thiazolidinones by using DCC catalyst and THF solvent in room temperature. In another study which was reported in 2013, Foroughifar et al. could synthesize 1,3-thiazolidin-4-ones at 70°C in solvent-free conditions by using Bi(SCH2COOH)3 as a catalyst [28]. In another work reported in 2016, Safaei-Ghomi et al. fabricated novel derivatives of these compounds by using nano-sized CdZr4(PO4)6 catalyst under ultrasonic irradiation [29]. Herein, we decide to fabricate innovative derivatives of 1,3-thiazolidin-4-one in agreement with green chemistry. The schematic illustration of the synthesis route is exhibited in Scheme 1. As presented in Figure 1, LDHs@PpPDA [30] was utilized as a catalyst for this reaction and the advantages of this is its facile synthetic steps, available raw materials, recyclability and cost-efficiency.