2-Amino-5-bromopyridinium 3-carboxy-4-hydroxybenzenesulfonate

Hemamalini, Madhukar; Fun, Hoong‐Kun

doi:10.1107/s1600536810033908

Cited by 2 publications

(2 citation statements)

References 16 publications

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“…In addition, the crystal structure of the C 7 H 5 O 6 S − and 2,3-diaminopyridinium ion pair has also been reported [24]. Moreover, a few other structures with 2-aminopyridinium ion [13] and its derivatives substituted by chloro [25,26], bromo [27] or methyl [28] group can be found in the CSD. For 2,6-diamino-9H-purin-1-ium cation, only its salts with 2-(2carboxylatophenyl)acetate and closo-dodecafluorododecaborate (B 12 F 12 2− ) anions have been described [29,30].…”

Section: Introductionmentioning

confidence: 93%

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

Bojarska,

Łyczko,

Mieczkowski

2024

Crystals

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A series of novel salts of heterocyclic polyamines with 5-sulfosalicylic acid (C4H7N4+)(C7H5O6S−)∙2(H2O) (1), (C4H6ClN4+)(C7H5O6S−)∙H2O (2), (C5H8N3+)(C7H5O6S−)∙H2O (3), (C5H7N6+)(C7H5O6S−)∙H2O (4), (C6H14N22+)(C7H4O6S2−)∙H2O (5), and (C14H19N2+)(C7H5O6S−) (6) have been successfully synthesized. Their crystal structures have been determined by single-crystal X-ray diffraction. Overall, compounds adopt a layered structure with aminium cations and 5-sulfosalicylic anions linked via water molecules. The solid-state architectures of these compounds are dominated by O(N,H)-H⋯O and N-H⋯N hydrogen bonds and stabilized by weak interconnects. C-Cl⋯π and S-O⋯π interactions, apart from π⋯π and C-H(O)⋯π, were reported. Diverse approaches were used to study the effect of substituents in the polyamines in solid-state arrangement. A Hirshfeld surface analysis, with associated 3D Hirshfeld surface maps and 2D fingerprint plots, molecular electrostatic potential, and energy frameworks were used to comprehensively investigate the nature and hierarchy of non-covalent interactions and inspect supramolecular differences. The contact enrichment ratio calculations provided deeper insight into the propensity of interconnects to influence crystal packing. The evaluation of the effects of H-bonding synthons resulting from different substituents in the polyamines on self-assemblies is also presented. In the context of crystal engineering, a specific intramolecular synthon via O-H⋯O observed in nearly all crystals can be employed in the pseudo-cyclic replacement strategy in the design of new molecules.

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Section: Introductionmentioning

confidence: 93%

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

Bojarska,

Łyczko,

Mieczkowski

2024

Crystals

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“…Bu çalışmada, 5-sülfosalisilik asit ile 2aminopiridin (ap), 2,3-diaminopiridin (23dap), 2mino-5-bromopiridin (2a5Brp) ve 2-amino-5kloropiridin (2a5Clp) proton transfer tuzları (ssa2ap [23], ssa23dap [24], ssa2a5Brp [25]…”

Section: Introductionunclassified

5-Sülfosalisik Asit İle 2-Aminopiridin Türevlerinin Proton Transfer Tuzlarının Antimikrobiyal Aktivitelerinin İncelenmesi

2023

International Conference on Innovative Academic Studies

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kan proteinleri için bir sabitleme maddesi, idrar proteini için bir ölçüm aracı ve enzim inhibisyonu olarak kullanılmaktadır. 5-Sülfosalisilik asit ve iyonlaşmış formları (H2ssa -, Hssa 2ve ssa 3-) ile birçok çalışma yapılmaktadır. 2-Aminopiridin türevlerinin farmakolojik etkileri arasında antihistaminik, antibakteriyel, antiviral, antiparazitik, anti-alzheimer, kardiyotonik, antifungal, antiinflamatuar, antikonvülsan ve analjezik özellikler yer alır. 2-Aminopiridinler piroksikam, tenoksikam, sülfasalazin, sülfapiridin, tripelenamin ve delavirdin ilaçlarının üretiminde kullanılır. Bu çalışmada, 5sülfosalisilik asit ile 2-aminopiridin, 2,3-diaminopiridin, 2,3-diamino-5-bromopiridin ve 2,3-diamino-5kloropiridin'in proton transfer tuzları literatürde bulunan yöntemlerle sentezlenmiştir. Başlangıç maddeleri ve proton transfer tuzlarının Listeria monocytogenes (ATCC 7644), Enterococcus faecalis (ATCC 29212), Bacillus subtilis, Staphylococcus aureus (NRRL-B 767) (Gram pozitif), Escherichia coli (ATCC 25922) ve Pseudomonas aeruginosa (ATCC 27853) (Gram negatif) bakterilerine ve Candida Albicans (ATCC 14053) mayasına karşı antibakteriyel ve anti fungal aktiviteleri incelenmiştir. Antifungal aktiviteler Flukonazol ile kıyaslanırken, antibakteriyel aktiviteleri ise Sefepim, Levofloksasin ve Vankomisin ile kıyaslanmıştır. Deneyde kullanılan ve sentezlenen bileşikler bakteri ve mayalara karşı aktiviteye sahip olduğu gözlenmiştir.

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2-Amino-5-bromopyridinium 3-carboxy-4-hydroxybenzenesulfonate

Cited by 2 publications

References 16 publications

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

5-Sülfosalisik Asit İle 2-Aminopiridin Türevlerinin Proton Transfer Tuzlarının Antimikrobiyal Aktivitelerinin İncelenmesi

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