Crystal structure of (1<i>S</i>,4<i>S</i>)-2,5-diazoniabicyclo[2.2.1]heptane dibromide

Britvin, Sergey N.; Rumyantsev, Andrey M.

doi:10.1107/s2056989017015870

Cited by 4 publications

(9 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the extra CH 2 in homopiperazine confers flexibility to the heterocyclic ring that allows it to explore a range of conformations in which the N–N distance varies from ∼2.75 Å in a U-shaped analogue of 1 to 3.05 in 1 itself and 3.20–3.28 Å in other examples where there are crystal structure data available. , As will be discussed, this conformational plasticity can be beneficial in the design of biologically active molecules. For the purpose of comparison, the N–N distance in 2,5-diazabicyclo[2.2.1]heptane is similar to piperazine, but this is extended to 4.28 Å in 4-aminopiperidine and 2,4,5,6-tetrahydropyrrolo[3,4- c ]pyrazole (Figure ), all of which have been explored as potential bioisosteres of piperazine. , …”

Section: Introductionmentioning

confidence: 99%

“…N–N distances for piperazine, 2,5-diazabicyclo[2.2.1]heptane, homopiperazine, 4-aminopiperidine, and 2,4,5,6-tetrahydropyrrolo[3,4- c ]pyrazole abstracted from single-crystal X-ray structural data. ,,, …”

Section: Introductionmentioning

confidence: 99%

“…For the purpose of comparison, the N−N distance in 2,5diazabicyclo[2.2.1]heptane is similar to piperazine, but this is extended to 4.28 Å in 4-aminopiperidine and 2,4,5,6tetrahydropyrrolo [3,4-c]pyrazole (Figure 2), all of which have been explored as potential bioisosteres of piperazine. 17,18 The basicity of piperazine can be a critical determinant of biological activity, dependent on the specific biochemical target. The pK a values of the conjugate acids of piperazine have been determined to be 5.35 and 9.73, which compare to values of 10.41 for homopiperazine and 11.2 for the more basic piperidine heterocycle.…”

Section: Introductionmentioning

confidence: 99%

“…N−N distances for piperazine, 2,5-diazabicyclo[2.2.1]heptane, homopiperazine, 4-aminopiperidine, and 2,4,5,6-tetrahydropyrrolo [3,4c]pyrazole abstracted from single-crystal X-ray structural data. 13,14,17,18 Figure 3. Single-crystal X-ray structural data for (A) piperazine (ITIZOA), (B) 2,5-diazabicyclo[2.2.1]heptane dihydrobromide salt (XENQIT), and (C) homopiperazine (AREBUX) with the measured N−N distances depicted.…”

Section: Introductionmentioning

confidence: 99%

“…Single-crystal X-ray structural data for (A) piperazine (ITIZOA), (B) 2,5-diazabicyclo[2.2.1]heptane dihydrobromide salt (XENQIT), and (C) homopiperazine (AREBUX) with the measured N−N distances depicted. 13,14,17…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Applications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 1

Meanwell

Loiseleur

2022

J. Agric. Food Chem.

View full text Add to dashboard Cite

Piperazine and homopiperazine are well-studied heterocycles in drug design that have found gainful application as scaffolds and terminal elements and for enhancing the aqueous solubility of a molecule. The optimization of drug candidates that incorporate these heterocycles in an effort to refine potency, selectivity, and developability properties has stimulated the design and evaluation of a wide range of bioisosteres that can offer advantage. In this review, we summarize the design and application of bioisosteres of piperazine and homopiperazine that have almost exclusively been in the drug design arena. While there are ∼100 approved drugs that incorporate a piperazine ring, only a single marketed agricultural product is built on this heterocycle. As part of the review, we discuss some of the potential reasons underlying the relatively low level of importance of this heterocycle to the design of agrochemicals and highlight the potential opportunities for their use in contemporary research programs.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Applications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 1

Meanwell

Loiseleur

2022

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

Alkali Metal Organic–Inorganic Hybrid Compounds with Different Crystal Dimensions Show Phase-Transition, Dielectric, and SHG Properties Based on a Quasi-Spherical Amine (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane

Guo,

Yang,

et al. 2023

Inorg. Chem.

View full text Add to dashboard Cite

Reactions of a chiral and quasi-spherical molecule [1S,4S-2,5−2.2.1-H 2 dabch]I 2 (1) with alkali metal halide MX (M = Na, K, Cs; X = Cl, Br) at room temperature produced a series of organic−inorganic hybrid (OIH) materials 4). The single-crystal X-ray diffraction analysis revealed that the organic−inorganic framework structures comprised of the templating ligand and alkali metal halides (NaBr, CsCl, KBr) displayed dimensions spanning from one-dimensional (1D) to three-dimensional (3D). Moreover, the results of both differential scanning calorimetry (DSC) and dielectric measurements demonstrated that compounds 1−4 displayed reversible, high-temperature phase transitions and noticeable dielectric anomalies. In addition, the temperature-dependent second harmonic generation (SHG) results revealed crystals 1 and 3 can switch from the SHG-ON to the SHG-OFF state, which was proved by the variable-temperature X-ray diffraction. This research aims to streamline the exploration of multifunctional second harmonic generation (SHG) and dielectric materials that have been synthesized using chiral ligands and alkali metals. This will provide researchers with enhanced opportunities to delve further into this specific research domain.

show abstract

Modifications in the piperazine ring of nucleozin affects anti-influenza activity

Correa-Padilla

Hernández-Cano

Cuevas

et al. 2022

Preprint

View full text Add to dashboard Cite

The infection caused by influenza virus is a latent tret, to contribute on the advancement of the discovery and design of nucleozin analogs, a molecule with antiinfluenza activity, we analyzed nucleozin analogs with modifications in the piperazine system, which leads to molecules with larger conformational freedom. Following a new nucleozin synthetic strategy, we obtained three new nucleozin analogs, and two of them were biologically evaluated in vitro and were less active than nucleozin. The loss of activity in the more flexible molecules highlights the need for the piperazine ring to maintain the activity of nucleozin analogues. Interestingly, this coincides with a QSAR model developed here for the prediction of the anti-influenza activity. The proposed model, along with the synthetic route, will be useful for further development of nucleozin analogues with antiviral activity.

show abstract

Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide

Cited by 4 publications

References 55 publications

Applications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 1

Applications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 1

Alkali Metal Organic–Inorganic Hybrid Compounds with Different Crystal Dimensions Show Phase-Transition, Dielectric, and SHG Properties Based on a Quasi-Spherical Amine (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane

Modifications in the piperazine ring of nucleozin affects anti-influenza activity

Contact Info

Product

Resources

About