Recent Advances in the Synthesis and Application of Tetrazoles

Cui, Lingling; Damu, Guri L.V.; Guri, L V; Zhou, Changtai

doi:10.6023/cjoc201208036

Cited by 31 publications

(8 citation statements)

References 55 publications

(57 reference statements)

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“…(4) Structural modifications in side chains of triazole ring by a variety of biologically important structural fragments including other azole rings [7] like imidazole [81], tetrazole [345], oxazole [178], benzimidaozle [129,130] etc. will still be a highly prevalent pathway to access 1,2,4-triazole derivatives with novel chemical structures and variable properties.…”

Section: Resultsmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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Section: Resultsmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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“…唑类化合物是一类重要而特殊的杂环, 包括五元唑杂环(如咪唑类 [20] 、吡唑类 [21] 、噻唑类 [22] 、噁唑类 [23] 、三唑类 [24,25] 、四唑类 [26] 等)及其稠合唑杂环(如苯并噻唑类 [27] 、苯并咪唑类 [28,29] 、苯并三唑类 [30] 、咔唑类 [31,32] 等), 含有氮、氧和/或硫等多个杂原子, 具有芳香性和丰富的电子, 这种奇特结构不仅易通过多种非共价键力如配位键、氢键、范德华力、π-π 堆积、疏水与静电作用等多种非共价键…”

Section: 超分子化学是一个高度交叉的活跃研究领域在化学unclassified

Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

Cheng¹,

Wang²,

Addla³

et al. 2016

Chin. J. Org. Chem.

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Noncovalent bond forces-based supramolecular chemistry grows quite rapidly and has been revealed to have extensively potential applications and huge development values in chemistry, physics, materials and information science, medicine and so on. Azole compounds such as imidazoles, thiazoles, oxazoles, pyrazoles, triazoles, tetrazoles and carbazoles containing special nitrogen aromatic heterocyclic structure, can exert non-covalent forces to form supramolecular complexes with inorganic and/or organic compounds and exhibit broad biological activity. In recent years, heterocyclic azole-based supramolecular complexes have been expeditiously expanding in the field of medicine, and have become a quite hot topic. Combined with our work and referring to other literature in recent 5 years, this paper systematically reviews the researches and applications of azole-based supermolecules as medicinal agents including anticancer, antibacterial, antifungal, antiparasitic, antidiabetic, antihypertensive, anti-inflammatory drugs and other ones. Finally, the perspectives of the future development of azole-based supermolecules as medicinal agents are also presented.

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“…Structural changes and the basic interactions identified from the 1,3,4‐oxadiazole scaffold, such as Sulfisoxazole (antibacterial), Oxacillin (antibiotic), Linezolid (antibacterial), Toloxatone (antidepressant), Furazolidone (antibacterial), Raltegravir (anti‐HIV) as shown in Figure . Oxadiazole compounds as the bioisostere of benzimidazoles and thiazoles, imidazoles, tetrazoles, and triazoles have attracted increasing attention. Recently, numerous researches have been devoting to oxadiazole compounds as a medicinal agent with an intent to discover novel chemical scaffold compounds with low toxicity, high bioactive and excellent pharmacokinetic property .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of 2‐(2‐Bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole Derivatives as Possible Anti‐Breast Cancer Agents

Ananth

Manikandan²,

Rajan³

et al. 2020

Chemistry & Biodiversity

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Breast Cancer (BCa) is the most often diagnosed cancer among women who were in the late 1940’s. Breast cancer growth is largely dependent on the expression of estrogen and progesterone receptor. Breast cancer cells may have one, both, or none of these receptors. The treatment for breast cancer may involve surgery, hormonal therapy (Tamoxifen, an aromatase inhibitor, etc.) and oral chemotherapeutic drugs. The molecular docking technique reported the findings on the potential binding modes of the 2‐(2‐bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole derivatives with the estrogen receptor (PDB ID: 3ERT). The 1,3,4‐oxadiazole derivatives 4a–4j have been synthesized and described by spectroscopic method. 2‐(2‐Bromo‐6‐nitrophenyl)‐5‐(4‐bromophenyl)‐1,3,4‐oxadiazole (4c) was reconfirmed by single‐crystal XRD. All the compounds have been tested in combination with generic Imatinib pharmaceutical drug against breast cancer cell lines isolated from Caucasian woman MCF‐7, MDA‐MB‐453 and MCF‐10A non‐cancer cell lines. The compounds with the methoxy (in 4c) and methyl (in 4j) substitution were shown to have significant cytotoxicity, with 4c showing dose‐dependent activation and decreased cell viability. The mechanism of action was reported by induced apoptosis and tested by a DNA enzyme inhibitor experiment (ELISA) for Methyl Transferase. Molecular dynamics simulations were made for hit molecule 4c to study the stability and interaction of the protein−ligand complex. The toxicity properties of ADME were calculated for all the compounds. All these results provide essential information for further clinical trials.

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Recent Advances in the Synthesis and Application of Tetrazoles

Cited by 31 publications

References 55 publications

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

Design, Synthesis, and Biological Evaluation of 2‐(2‐Bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole Derivatives as Possible Anti‐Breast Cancer Agents

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