“…The most active compounds, 19a and 19b, have IC 50 values of 0.24 M, 0.31 M, 1.67 M, and 1.90 M, 0.17 M, and 1.45 M, respectively, against MCF-7, A549, and A375 cell lines. Chakrapani et al ( 2018 ) and co-workers have described the design and synthesis of a new 1,2,4-oxadiazole linked imidazothiadiazole analogue that is structurally close to levamisole (Chakrapani et al 2018 ). Anticancer activity data was generated for these compounds using the MTT assay for three human cell lines: A375, MCF-7, and human renal carcinoma cell line (ACHN) (Table S4 ).…”
The 5-membered oxadiazole and thiadiazole scaffolds are the most privileged and well-known heterocycles, being a common and essential feature of a variety of natural products and medicinal agents. These scaffolds take up the center position and are the core structural components of numerous drugs that belong to different categories. These include antimicrobial, anti-tubercular, anti-inflammatory, analgesic, antiepileptic, antiviral, and anticancer agents. In this review, we mostly talk about the isomers 1,2,4-oxadiazole and 1,3,4-thiadiazole because they have important pharmacological properties. This is partly because they are chemical and heat resistant, unlike other isomers, and they can be used as bio-isosteric replacements in drug design. We are reviewing the structural modifications of different oxadiazole and thiadiazole derivatives, more specifically, the anti-tubercular and anticancer pharmacological activities reported over the last 5 years, as we have undertaken this as a core area of research. This review article desires to do a thorough study and analysis of the recent progress made in the important biological isomers 1,2,4-oxadiazole and 1,3,4-thiadiazol. This will be a great place to start for future research.
Key points
• Five-membered heterocyclic compound chemistry and biological activity recent survey.
• Synthesis and pharmacological evolution of 1,2,4-oxadiazole and 1,3,4-thiadiazole are discussed in detail.
• The value and significance of heterocyclic compounds in the field of drug designing are highlighted.
Supplementary Information
The online version contains supplementary material available at 10.1007/s00253-022-11969-0.
“…The most active compounds, 19a and 19b, have IC 50 values of 0.24 M, 0.31 M, 1.67 M, and 1.90 M, 0.17 M, and 1.45 M, respectively, against MCF-7, A549, and A375 cell lines. Chakrapani et al ( 2018 ) and co-workers have described the design and synthesis of a new 1,2,4-oxadiazole linked imidazothiadiazole analogue that is structurally close to levamisole (Chakrapani et al 2018 ). Anticancer activity data was generated for these compounds using the MTT assay for three human cell lines: A375, MCF-7, and human renal carcinoma cell line (ACHN) (Table S4 ).…”
The 5-membered oxadiazole and thiadiazole scaffolds are the most privileged and well-known heterocycles, being a common and essential feature of a variety of natural products and medicinal agents. These scaffolds take up the center position and are the core structural components of numerous drugs that belong to different categories. These include antimicrobial, anti-tubercular, anti-inflammatory, analgesic, antiepileptic, antiviral, and anticancer agents. In this review, we mostly talk about the isomers 1,2,4-oxadiazole and 1,3,4-thiadiazole because they have important pharmacological properties. This is partly because they are chemical and heat resistant, unlike other isomers, and they can be used as bio-isosteric replacements in drug design. We are reviewing the structural modifications of different oxadiazole and thiadiazole derivatives, more specifically, the anti-tubercular and anticancer pharmacological activities reported over the last 5 years, as we have undertaken this as a core area of research. This review article desires to do a thorough study and analysis of the recent progress made in the important biological isomers 1,2,4-oxadiazole and 1,3,4-thiadiazol. This will be a great place to start for future research.
Key points
• Five-membered heterocyclic compound chemistry and biological activity recent survey.
• Synthesis and pharmacological evolution of 1,2,4-oxadiazole and 1,3,4-thiadiazole are discussed in detail.
• The value and significance of heterocyclic compounds in the field of drug designing are highlighted.
Supplementary Information
The online version contains supplementary material available at 10.1007/s00253-022-11969-0.
“…Chakrapani et al [ 52 ] developed 3-(6-chloro-2-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)-5-(substituted phenyl)-1,2,4-oxadiazole by using Scheme 10 . The antitumor activity of the synthesized derivatives was evaluated by MTT assay against ACHN (renal), MCF-7 (breast), and A375 (melanoma) tumor cell line using doxorubicin as a reference standard.…”
Section: Antitumor Activitymentioning
confidence: 99%
“…The compound 16j exhibits excellent activity towards melanoma cancer cell line (A375) and potent activities towards MCF- 7 and ACHN cancer cell lines. The results of the antitumor activity of synthesized derivatives were presented in (Table 10 , Chakrapani et al [ 52 ]). Scheme 10 Synthesis of 1,2,4-oxadiazole derivatives …”
Section: Antitumor Activitymentioning
confidence: 99%
“…The compound 16j exhibits excellent activity towards melanoma cancer cell line (A375) and potent activities towards MCF-7 and ACHN cancer cell lines. The results of the antitumor activity of synthesized derivatives were presented in(Table 10, Chakrapani et al[52]). Gudipati et al[53] developed (Z)-3-[(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) imino]-5 or 7-substituted indolin-2-one (Scheme 11) and evaluated for antitumor activity by MTT assay against MCF-7, IMR-32, and HeLa tumor cell lines using cisplatin as a reference standard.…”
As we know that, Oxadiazole or furadi azole ring containing derivatives are an important class of heterocyclic compounds. A heterocyclic five-membered ring that possesses two carbons, one oxygen atom, two nitrogen atoms, and two double bonds is known as oxadiazole. They are derived from furan by the replacement of two methylene groups (= CH) with two nitrogen (-N =) atoms. The aromaticity was reduced with the replacement of these groups in the furan ring to such an extent that it shows conjugated diene character. Four different known isomers of oxadiazole were existed such as 1,2,4-oxadiazole, 1,2,3-oxadiazole, 1,2,5-oxadiazole & 1,3,4-oxadiazole. Among them, 1,3,4-oxadiazoles & 1,2,4-oxadiazoles are better known and more widely studied by the researchers due to their broad range of chemical and biological properties. 1,3,4-oxadiazoles have become important synthons in the development of new drugs. The derivatives of the oxadiazole nucleus (1,3,4-oxadiazoles) show various biological activities such as antibacterial, anti-mycobacterial, antitumor, anti-viral and antioxidant activity, etc. as reported in the literature. There are different examples of commercially available drugs which consist of 1,3,4-oxadiazole ring such as nitrofuran derivative (Furamizole) which has strong antibacterial activity, Raltegravir as an antiviral drug and Nesapidil drug is used in anti-arrhythmic therapy. This present review summarized some pharmacological activities and various kinds of synthetic routes for 2, 5-disubstituted 1,3,4-oxadiazole, and their derived products.
“…Two of the obtained compounds 13a-b (Table 2) showed good antitumor activity with the IC 50 values between 0.11-1.47 µM against the aforementioned cancer cell lines. Interestingly, the reference compound exhibited similar or slightly lower anticancer activity (the IC 50 values in the range of 0.79 to 5.51 µM) [70].…”
Five-membered 1,2,4-oxadiazole heterocyclic ring has received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the novel drug development. After a century since the 1,2,4-oxadiazole have been discovered, the uncommon potential attracted medicinal chemists’ attention, leading to the discovery of a few presently accessible drugs containing 1,2,4-oxadiazole unit. It is worth noting that the interest in a 1,2,4-oxadiazoles’ biological application has been doubled in the last fifteen years. Herein, after a concise historical introduction, we present a comprehensive overview of the recent achievements in the synthesis of 1,2,4-oxadiazole-based compounds and the major advances in their biological applications in the period of the last five years as well as brief remarks on prospects for further development.
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