N-Phenyl-2-pyridinecarbothioamides as gastric mucosal protectants

Kinney, William A.; Lee, Nancy E.; Blank, Robert M.; Demerson, Christopher A.; Sarnella, Carol S.; Scherer, Noreen T.; Mir, G.N.; Borella, Luis E.; DiJoseph, John F.; Wells, Cheryl

doi:10.1021/jm00163a053

Cited by 21 publications

(12 citation statements)

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“…Bioactive PCAs can act as S,N‐bidentate ligands to metal ions to give access to a library of organometallic and coordination compounds . We functionalized a PCA ligand with a sulfonamide moiety, a motif found in many drugs and one that is involved in interactions with the active sites of CAs.…”

Section: Resultsmentioning

confidence: 99%

“…Bioactive PCAs can act as S,N-bidentate ligands to metal ions to give access to al ibrary of organometallic and coordination compounds. [25,30,31] We functionalized aP CA ligand with as ulfonamide moiety,amotif found in many drugsa nd one that is involved in interactions with the active sites of CAs. The sulfonamide-substituted PCA N-(4-sulfamoylphenyl)pyridine-2-carbothioamide (1)w as prepared in ao ne-pot synthesis by heating p-phenylenediamine sulfanilamide and elemental sulfur in 2-picoline at reflux for 18 hw ith ac atalytic amount of sodiums ulfide (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

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Organoruthenium and Organoosmium Complexes of 2‐Pyridinecarbothioamides Functionalized with a Sulfonamide Motif: Synthesis, Cytotoxicity and Biomolecule Interactions

et al. 2018

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Anticancer‐active RuII–η6‐p‐cymene complexes of bioactive 2‐pyridinecarbothioamide ligands have been shown to have high selectivity for plectin and can be administered orally. Reported herein is the functionalization of a 2‐pyridinecarbothioamide with a sulfonamide group and its conversion into M–η6‐p‐cymene complexes (M = Ru, Os). The presence of a sulfonamide moiety in many organic drugs and metal complexes endows these agents with interesting biological properties and can transform the latter into multi‐targeted agents. The compounds were characterized with standard methods and the in vitro anticancer activity data was compared with studies on the hydrolytic stability of the complexes and their reactivity to small biomolecules. A molecular modeling study revealed plausible modes of binding of the complexes in the catalytic pocket of carbonic anhydrase II.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Organoruthenium and Organoosmium Complexes of 2‐Pyridinecarbothioamides Functionalized with a Sulfonamide Motif: Synthesis, Cytotoxicity and Biomolecule Interactions

et al. 2018

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“…Anticancer activities of ruthenium(II) compounds based on N-substituted 2-pyridinecarbothioamides (PCAs) (25) have been documented in the literature (Figure 17) [80]. The 2-pyridinecarbothioamide ligands have previously shown notable activity as gastric mucosal protectants and low acute toxicity in vivo [81]. However, their coordination Ru Cl to ruthenium(II) yielded highly cytotoxic agents in the more chemoresistant SW480 (colon adenocarcinoma) and A549 cell lines.…”

Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes

Motswainyana

Ajibade

2015

Advances in Chemistry

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Ruthenium compounds are highly regarded as potential drug candidates. The compounds offer the potential of reduced toxicity and can be tolerated in vivo. The various oxidation states, different mechanism of action, and the ligand substitution kinetics of ruthenium compounds give them advantages over platinum-based complexes, thereby making them suitable for use in biological applications. Several studies have focused attention on the interaction between active ruthenium complexes and their possible biological targets. In this paper, we review several ruthenium compounds which reportedly possess promising cytotoxic profiles: from the discovery of highly active compounds imidazolium [trans-tetrachloro(dmso)(imidazole)ruthenate(III)] (NAMI-A), indazolium [trans-tetrachlorobis(1H-indazole)ruthenate(III)](KP1019), and sodium trans-[tetrachloridobis(1H-indazole)ruthenate(III)] (NKP-1339) to the recent work based on both inorganic and organometallic ruthenium(II) compounds. Half-sandwich organometallic ruthenium complexes offer the opportunity of derivatization at the arene moiety, while the three remaining coordination sites on the metal centre can be functionalised with various coordination groups of various monoligands. It is clear from the review that these mononuclear ruthenium(II) compounds represent a strongly emerging field of research that will soon culminate into several ruthenium based antitumor agents.

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“…: m/z (%) = 330 (50), 298 (25), 297 (100), 282 (14). HRMS (EI): m/z calcd for C 21 H 18 N 2 S: 330.1191; found: 330.1187.…”

Section: Ms (Ei)mentioning

confidence: 99%

A New Approach to the Synthesis of 1-Arylbenzimidazole-2-thiones from Nitroarenes and Anilines through Halogen-Free Substitution of Hydrogen via Iminophosphorane Intermediates

Łukasik

Wróbel

2015

Synthesis

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2-(Arylamino)phenyliminophosphoranes, formed directly from 2-nitrosodiarylamines, undergo a high-yielding cyclocondensation with CS 2 , providing a variety of 1-arylbenzimidazole-2-thiones. The reaction concludes a new synthetic route leading to the title compounds from simple nitroarenes and arylamines. The protocol is superior to common methods that use N-arylarylenediamines because it omits the S N Ar substitution of halogen atoms in ortho-halonitroarenes, as well as reduction processes required for the synthesis of the intermediate diamines.

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N-Phenyl-2-pyridinecarbothioamides as gastric mucosal protectants

Cited by 21 publications

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Organoruthenium and Organoosmium Complexes of 2‐Pyridinecarbothioamides Functionalized with a Sulfonamide Motif: Synthesis, Cytotoxicity and Biomolecule Interactions

Organoruthenium and Organoosmium Complexes of 2‐Pyridinecarbothioamides Functionalized with a Sulfonamide Motif: Synthesis, Cytotoxicity and Biomolecule Interactions

Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes

A New Approach to the Synthesis of 1-Arylbenzimidazole-2-thiones from Nitroarenes and Anilines through Halogen-Free Substitution of Hydrogen via Iminophosphorane Intermediates

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