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High-Performance Liquid Chromatography
Published in Adorjan Aszalos, Modern Analysis of Antibiotics, 2020
Joel J. Kirschbaum, Adorjan Aszalos
Cefatrizine was quantified in serum and urine using an octadecylsilane column with a mobile phase of 0.03 M sodium phosphate buffer, pH 5-methanol (80:20) flowing at 1 ml/min through a 254 nm detector [220]. The limit of detection was approximately 1–2 µg/ml serum or urine using cephradine as internal standard. These same investigators improved the detection system by using postcolumn derivatization with fluorescamine and fluorescent detection at 387 nmex/480 nmem [221]. This modification gave a 10-fold increase in sensitivity, with excellent linearity in the ranges of 0.1–1 µg/ml and 10–100 µg/ml.
Cefadroxil, Cephaloridine, Cephacetrile, Cephapirin, Cephradine, and Other Rarely Used First-Generation Cephalosporins
Published in M. Lindsay Grayson, Sara E. Cosgrove, Suzanne M. Crowe, M. Lindsay Grayson, William Hope, James S. McCarthy, John Mills, Johan W. Mouton, David L. Paterson, Kucers’ The Use of Antibiotics, 2017
The most commonly used first-generation cephalosporins are the parenteral cephalosporins, cefazolin and cephalothin (see Chapter 18, Cephalothin and cefazolin), and the oral drug, cephalexin (See Chapter 19, Cephalexin). However, a number of other first-generation cephalosporins have been available for clinical use in some countries, although are rarely used now. These include cefadroxil, cephradine, cephapirin, cephacetrile, cephaloridine, cephaloglycin, cephalonium, cefatrizine, cefazaflur, cefazedone, cefroxadine, and cephtazole. Specific comments will be made about some of these first-generation cephalosporins.
New 1,2,3-triazole linked ciprofloxacin-chalcones induce DNA damage by inhibiting human topoisomerase I& II and tubulin polymerization
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Hamada H. H. Mohammed, Amer Ali Abd El-Hafeez, Kareem Ebeid, Aml I. Mekkawy, Mohammed A. S. Abourehab, Emad I. Wafa, Suhaila O. Alhaj-Suliman, Aliasger K. Salem, Pradipta Ghosh, Gamal El-Din A. Abuo-Rahma, Alaa M. Hayallah, Samar H. Abbas
Furthermore, 1,2,3-Triazoles are essential scaffolds in medicinal chemistry that are widely used in many drug-design protocols as bio-isosteres of ester, amide, and other heterocycles44,45. Compounds containing 1,2,3-triazole heterocycle can form different non-covalent interactions such as hydrogen bonds, dipole-dipole bonds, hydrophobic interactions, and van der Waals forces with various biological targets, thus they possess various biological effects (e.g., anticancer46–49, antibacterial50,51, antifungal52,53, antiviral54,55, antimalarial56,57, and antitubercular58,59 activities). Additionally, 1,2,3-Triazole is a favourable basic unit in the finding of new anticancer agents, and some of its derivatives have now been in clinics or under clinical trials for combating against cancers45. 1,2,3‐Triazoles exhibited their anticancer effects via different modes of action. They exerted their anti-proliferative effects through Tubulin polymerisation inhibition or inhibition of some kinases such as epidermal growth factor receptor, c-Met Kinase, and vascular endothelial growth factor. They also caused inhibition of vital enzymes such as aromatase, tryptophan 2,3‐dioxygenase, carbonic anhydrases, and thymidylate synthase60. Also, many drugs have 1,2,3-triazole moiety, such as cefatrizine IV, seviteronel V, carboxyamidotriazole VI, and mubritinib VII entered active clinical trials in 2021 (Figure 2)61.
Application of triazoles in the structural modification of natural products
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2021
Hong-Yan Guo, Zheng-Ai Chen, Qing-Kun Shen, Zhe-Shan Quan
Many marketed drugs contain heterocycles, and triazoles with a five-membered ring composed of two carbon atoms and three nitrogen atoms exist in different heterocycles There are two types of triazole – 1,2,3-triazole and 1,2,4-triazole (Figure 1)9. Triazole can be readily obtained, and the framework can act as an amide, ester, carboxylic acid, and other heterocycles such as pyrazole isosteres10. By affecting the hydrogen bonding ability, polarity and lipophilicity of the molecules, the triazole moiety can improve the physicochemical properties, toxicology, pharmacokinetics and pharmacology of the compounds11,12. The synthetic moieties containing these molecular structures have been used extensively in the discovery of drugs due to their low occurrence in nature13.Meanwhile, on the basis of the literature, triazole and its derivatives have aroused enormous interest owing to their pharmaceutical and therapeutic applications, including their use as anticonvulsant14–17, antidepressant18, anticancer19–23, antiviral24, antimicrobial25–33, anti-acetylcholinesterase34, anti-inflammatory35,36, antioxidant37–40, antiparasitic41–43, and anti-diabetic drugs44. Their ability to produce various non-covalent interactions to improve solubility and binding to bimolecular targets may be the reason for this wide applicability45. Furthermore, a number of drugs that contain 1,2,3-triazole scaffolds, including TSAO46 (anti-HIV agent), Cefatrizine47 (an antibiotic), CAI48 (anti-cancer agent), and Tazobactum49 (anti-bacterial agent), are currently used in clinical applications (Figure 2). The favourable properties of the enhanced biological activities of the triazole ring include hydrogen bonding capability under in vivo conditions, a strong dipole moment, high chemical stability (they are typically inert for oxidising and reducing agents), and rigidity.33
The 1,2,3-triazole ‘all-in-one’ ring system in drug discovery: a good bioisostere, a good pharmacophore, a good linker, and a versatile synthetic tool
Published in Expert Opinion on Drug Discovery, 2022
Deniz Lengerli, Kübra Ibis, Yahya Nural, Erden Banoglu
Heterocycles are omnipresent ring systems in bioactive compounds, which are generally used to boost the potency by participating in complementary binding interactions or to optimize the ADME properties as well as may act as a scaffold to provide a platform for optimum spatial positioning of important functional groups attached to it [1–3]. Among them, the five-membered triazole ring has a widespread occurrence in the core structure of experimental compounds since it may serve as a base for a wide variety of substituents paving the way for building of novel bioactive chemical scaffolds [4]. In a five-membered ring system, the positional arrangement of nitrogen atoms generates two triazole regioisomers, namely, 1,2,3-triazole (ν-triazole) and 1,2,4-triazole (s-triazole). Compounds embedding the 1,2,4-triazole structure have long been exploited in the construction of bioactive scaffolds and nine FDA-approved drugs such as anastrozole, cefmetazole, fluconazole, itraconazole, letrozole, maraviroc, ribavirin, terconazole and voriconazole contain the 1,2,4-triazole core [3]. However, the prevailing occurrence of 1,2,3-triazole framework is rather new and has been gaining momentum in the past two decades [5–13] following the introduction of the ‘click’ chemistry concept by Kolb, Finn and Sharpless in 2001, which was a main breakthrough in triazole chemistry making a broad number of regioselective 1,2,3-triazole derivatives highly accessible [10]. Therefore, in the last two decades, the 1,2,3-triazole ring has enriched in the structural core of many bioactive compounds with a wide range of pharmacological activities such as anticancer [14–17], antidiabetic [18], anticonvulsant [19,20], antiviral [21], antimicrobial [22–26], antitubercular [27,28], antiplasmoidal and antimalarial [29] among others as thoroughly reviewed in recent publications [5,6]. However, only a few drugs carrying this ring such as older drugs (before 2001) tazobactam [30] and cefatrizine [31] along with the recently developed (after 2001) radezolid [32], rufinamide [33] and suvorexant [34] have entered medical use (Figure 1).