Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by S⋯O interaction

Садчикова, Е. В.; Бакулев, В. А.; Subbotina, Julia O.; Privalova, Darya L.; Dehaen, Wim; Hecke, Kristof Van; Robeyns, Koen; Meervelt, Luc Van; Mokrushin, V. S.

doi:10.1016/j.tet.2013.06.062

Cited by 9 publications

(7 citation statements)

References 33 publications

(36 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Acyl isothiocyanates are predominant bioactive compounds having many biological activities and are versatile precursors to the preparation of sulfur-containing heterocycles [1][2][3][4][5][6][7] .…”

Section: Introductionmentioning

confidence: 99%

Sebacoyl Isothiocyanate in the Synthesis of Bis (1,3,4-Thiadiazole, 1,3,4-Thiadiazolo[3,2-a]Pyridine, 4-Thiazolidinone, Chromenes, and Naphtho[1,2-b][1,4]Oxazine) Derivatives

Thabet¹

2020

Orient. J. Chem

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Sebacoyl Isothiocyanate in the Synthesis of Bis (1,3,4-Thiadiazole, 1,3,4-Thiadiazolo[3,2-a]Pyridine, 4-Thiazolidinone, Chromenes, and Naphtho[1,2-b][1,4]Oxazine) Derivatives

Thabet¹

2020

Orient. J. Chem

View full text Add to dashboard Cite

show abstract

“…While this statement may seem counterintuitive given that sulfur atoms also bear lone pairs and chemists are conditioned to avoid contorting molecules into shapes where lone pair/lone pair repulsion can occur, its validity is supported by extensive experimental and theoretical studies. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Here we shine light on the importance of intramolecular sulfur-lone pair interactions for the binding of small molecules, such as drugs, to receptors, such as enzymes, offering both a caution and a recommended procedure for properly modeling the binding of ligands where such effects might be at play.…”

Section: Introductionmentioning

confidence: 99%

The influence of intramolecular sulfur–lone pair interactions on small-molecule drug design and receptor binding

2016

View full text Add to dashboard Cite

Sulfur-lone pair interactions are important conformational control elements in sulfur-containing heterocycles that abound in pharmaceuticals, natural products, agrochemicals, polymers and other important classes of organic molecules. Nonetheless, the role of intramolecular sulfur-lone pair interactions in the binding of small molecules to receptors is often overlooked. Here we analyze the magnitudes and origins of these interactions for a variety of biologically relevant small molecules using quantum chemical and automated docking calculations. In most cases examined in this study, the lowest energy conformation of the small molecule displays a sulfur-lone pair close contact. However, docking studies, both published and new, often predict that conformations without sulfur-lone pair contacts have the best binding affinity for their respective receptors. This is a serious problem. Since many of these predicted bound conformations are not actually energetically accessible, pursuing design (e.g., drug design) around these binding modes necessarily will lead, serendipity aside, to dead end designs. Our results constitute a caution that one best not neglect these interactions when predicting the binding affinities of potential ligands (drugs or not) for hosts (enzymes, receptors, DNA, RNA, synthetic hosts). Moreover, a better understanding and awareness of sulfur-lone pair interactions should facilitate the rational modulation of host-guest interactions involving sulfur-containing molecules.

show abstract

“…The non bonded interaction was studied in terms of Weinhold covalence factors and AIM schemes (Scheme 88). [142] …”

Section: Synthesis Of 1235‐tetrazinementioning

confidence: 99%

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

et al. 2022

View full text Add to dashboard Cite

Heterocyclic compounds play a tremendous role in the field of medicinal chemistry due to their association with diverse pharmacological properties. Most of the pharmaceutical drugs used in medicines possess a wide range of heterocyclic nucleus. It was decided basis on literature studies that various synthetic protocols like microwave‐assisted, nanocatalysed, green synthesis, click reaction, and multicomponent routes could be used for the betterment of the purity of products, selectivity, and better yields of the products. We have focused attention on the development of synthetic strategies of the above‐mentioned moieties because N‐, O‐ and S‐ containing heterocyclic compounds have seemed owing to a wide diversity of their biological activities viz. antioxidant, anticancer, anticonvulsant, anti‐inflammatory, neuroprotective, antiproliferative, anti‐obesity, antihyperglycemic, antihypercholesteroler, antiulcer, antidiabetic, antileishmanial, antitrypanosomal, antibiotic, etc. In this review article, an overview of the applications of synthetic protocols for the preparation of five‐membered and six‐membered heterocyclic compounds containing two or more heteroatoms (O, N, S) at different‐different positions along with their different potent and competent candidates against various diseases is presented in last 10–15 years.

show abstract

Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by S⋯O interaction

Abstract: Cycloaddition reactions of 5‐diazopyrazoles and 5‐diazoimidazoles with acyl isothiocyanates give thiatriazine derivatives.

Cited by 9 publications

References 33 publications

Sebacoyl Isothiocyanate in the Synthesis of Bis (1,3,4-Thiadiazole, 1,3,4-Thiadiazolo[3,2-a]Pyridine, 4-Thiazolidinone, Chromenes, and Naphtho[1,2-b][1,4]Oxazine) Derivatives

Sebacoyl Isothiocyanate in the Synthesis of Bis (1,3,4-Thiadiazole, 1,3,4-Thiadiazolo[3,2-a]Pyridine, 4-Thiazolidinone, Chromenes, and Naphtho[1,2-b][1,4]Oxazine) Derivatives

The influence of intramolecular sulfur–lone pair interactions on small-molecule drug design and receptor binding

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

Contact Info

Product

Resources

About