Halogenated (F, Cl) 1,3-benzodiazoles, 1,2,3-benzotriazoles, 2,1,3-benzothia(selena)diazoles and 1,4-benzodiazines inducing Hep2 cell apoptosis

Prima, Darya O.; Vorontsova, Elena; Makarov, Arkady G.; Makarov, Alexander Yu.; Bagryanskaya, I. Yu.; Mikhailovskaya, Tatiana F.; Slizhov, Yuri G.; Zibarev, Andrey V.

doi:10.1016/j.mencom.2017.09.002

Cited by 19 publications

(11 citation statements)

References 31 publications

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“…The Fluorinated benzo‐fused 1,2,3‐triazoles ( 112 ) were synthesized by Makarov et al ., the cyclization of 1,2‐diaminobenzenes ( 111 ) (Scheme 14). The formed desired product was confirmed by various instrumental techniques like high‐resolution MS, multinuclear NMR, and X‐ray diffraction (XRD) [47–49] . By this protocol, the formed benzofused aza heterocyclic scaffolds and substituents F possess high cytotoxicity with high apoptotic activity at low concentrations.…”

Section: Five‐membered Heterocycles Having Three Nitrogen Atomsmentioning

confidence: 82%

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

et al. 2022

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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.

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Section: Five‐membered Heterocycles Having Three Nitrogen Atomsmentioning

confidence: 82%

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

et al. 2022

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“…The robustness of the {SnN … }2 synthon is illustrated in Fig. 5d for 21 [74], that is, a perchlorinated derivative. In this instance, the dimer forms in preference to putative Se … Cl interactions.…”

Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 99%

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

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“…The angle N1−Se1−N2 in our selenium(IV) complex is 93.9(1)°, while in 4,5,6,7-tetrachloro-2,1,3benzoselenadiazole, the N1−Se2−N3 angle is 94.34°. 95 In Figure 2, the structure of the 5,6-dichloro-2,1,3benzoselenadiazole dimer is depicted. Four atoms in the Se 2 N 2 moiety form a planar quadrilateral.…”

Section: Structure Descriptionmentioning

confidence: 99%

“…The asymmetric unit cell consists of the 4,5-dichloro- o -phenylenediamine ligand and selenium(IV) ion and is oriented in one plane; the Se1–N1(1.794(3)) distance is slightly longer than Se1–N2 (1.789(3)) in the same unit. Prima’s group obtained the series of 2,1,3-benzoselenadiazoles, that is, the planar molecule 4,5,6,7-tetrachloro-2,1,3-benzoselenadiazole, where they have reported similar Se–N bond distances: 1.792(3) Å and 1.779(3) Å for Se2–N1 and Se2–N3, respectively. The angle N1–Se1–N2 in our selenium(IV) complex is 93.9(1)°, while in 4,5,6,7-tetrachloro-2,1,3-benzoselenadiazole, the N1–Se2–N3 angle is 94.34° …”

Section: Structure Descriptionmentioning

confidence: 99%

“…Prima’s group obtained the series of 2,1,3-benzoselenadiazoles, that is, the planar molecule 4,5,6,7-tetrachloro-2,1,3-benzoselenadiazole, where they have reported similar Se–N bond distances: 1.792(3) Å and 1.779(3) Å for Se2–N1 and Se2–N3, respectively. The angle N1–Se1–N2 in our selenium(IV) complex is 93.9(1)°, while in 4,5,6,7-tetrachloro-2,1,3-benzoselenadiazole, the N1–Se2–N3 angle is 94.34° …”

Section: Structure Descriptionmentioning

confidence: 99%

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Experimental and Theoretical Studies of Dimers Stabilized by Two Chalcogen Bonds in the Presence of a N···N Pnicogen Bond

et al. 2021

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The structure of the 5,6-dichloro-2,1,3-benzoselenadiazole homodimer, obtained by adding the ligand, 4,5-dichloro-o-phenylenediamine, to the methanolic solution of SeCl4, was determined by X-ray crystallography, augmented by Fourier transform infrared, Raman, and NMR spectroscopy. The binding motif involves a pair of Se···N chalcogen bonds, with a supplementary N···N pnicogen bond. Quantum calculations provide assessments of the strengths of the individual interactions as well as their contributing factors. All together, these three bonds compose a total interaction energy between 5.4 and 16.8 kcal/mol, with the larger chalcogen atom associated with the strongest interactions. Replacement of the Se atoms by S and Te analogues allows analysis of the dependence of these forces on the nature of the chalcogen atom. Calculations also measure the importance to the binding of the presence of a second N atom on each diazole unit as well as the substituted phenyl ring to which it is fused.

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Halogenated (F, Cl) 1,3-benzodiazoles, 1,2,3-benzotriazoles, 2,1,3-benzothia(selena)diazoles and 1,4-benzodiazines inducing Hep2 cell apoptosis

Cited by 19 publications

References 31 publications

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

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

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Experimental and Theoretical Studies of Dimers Stabilized by Two Chalcogen Bonds in the Presence of a N···N Pnicogen Bond

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