Antiallergic agents. 3. N-(1H-tetrazol-5-yl)-2-pyridinecarboxamides

Honma, Yasushi; Hanamoto, Kyoji; Hashiyama, Tomiki; Sekine, Yasuo; Takeda, Mikio; Ono, Yasutoshi; Tsuzurahara, Kei

doi:10.1021/jm00368a005

Cited by 8 publications

(2 citation statements)

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“…Note that the N-substituted derivatives of (E)-azastilbenes are also known to possess a variety of biological activities; [19][20][21] in particular, all of the presently investigated compounds showed antimicrobial activity. 22 Experimental Compounds 1-9 were synthesized according to the literature.…”

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confidence: 94%

Photophysical properties of izomeric N-chlorobenzyl substituted (E)-2′ (3′-or 4′)-hydroxy-4-stilbazolium chlorides in alcohols

Prukała

Khmelinskii

et al. 2011

Phys. Chem. Chem. Phys.

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Absorption and steady-state fluorescence spectra of nine N-p-(m- and o-) chlorobenzyl substituted (E)-2'-(3' and 4')-hydroxy-4-stilbazolium chlorides belonging to the hemicyanine class of compounds were studied in extra dry alcohols of different polarity. Derivatives with 2'-hydroxy or 4'-hydroxy substituent in the benzene moiety of stilbazol molecule displayed negative solvatochromizm. On the other hand, the excited state decay of compounds with a 3'-hydroxy group in the benzene moiety was dominated by non-radiative processes in protic solvents. Solutions of each of the compounds are yellow in extra dry solvents, red in solvents with small amount of water and yellow again if more water is added. The absorbance and steady-state fluorescence methods were used to explain the protonation/deprotonation processes for N-p-chlorobenzyl-(E)-4'-hydroxy-4-stilbazolium chloride and its zwitterionic or quinoid form in 2-propanol responsible for these phenomena.

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confidence: 94%

Photophysical properties of izomeric N-chlorobenzyl substituted (E)-2′ (3′-or 4′)-hydroxy-4-stilbazolium chlorides in alcohols

Prukała

Khmelinskii

et al. 2011

Phys. Chem. Chem. Phys.

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“…First a Suzuki cross-coupling reaction of available arylboronic acids with 3-amino-6-chloropyridazine 3 described previously 25) was used to prepare 3-amino-6-arylpyridazine 6 with 12-60% yields. The acetamidopyridazine derivatives 5a-k were then prepared in 18-45% yields by coupling the activated 2-naphtylacetic acid with the 3-amino-6-arylpyridazine 6 using the diimidazolylcarbodiimide (DIC) procedure described by Honma et al 26) The derivatives 5 obtained above were evaluated for their affinity for the NPY 5 as well as the NPY 1 receptors. None of the prepared compounds exhibited significant affinity ( Table 2).…”

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confidence: 99%

A Convenient 3-Step Synthesis of 3-Acetamido-6-arylpyridazines Directed to Novel Y5 Receptor Antagonist.

Guéry¹,

Rival²,

Wermuth³

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Obesity is a common disorder in the industrialized world. The major environmental factor associated with the rising prevalence of obesity is an increasingly sedentary lifestyle, compounded by greater levels of caloric intake. Recent studies [1][2][3][4][5][6][7][8][9][10][11][12] have shown that in the central nervous system (CNS), neuropeptide Y (NPY) has been implicated in obesity and feeding, anxiety and depression, endocrine function and metabolism.1) More particularly it was observed that food intake was inhibited by antisense oligodeoxynucleotides to the NPY 5 receptors. 4)Therefore there is a great interest in the synthesis of NPY receptor antagonists acting as antagonists on NPY 5 receptors. Some potent and selective NPY 5 receptor antagonists have been described in the literature [13][14][15][16][17][18] and their affinities were assessed through in vitro data over transfected CHO cells. However for most of them no in vivo data were published, 19) this is the case for compound 1 (Fig. 1) which is active in vitro (IC 50 ϭ8.3 nM) but inactive in vivo. We hypothetized that the exchange of the pyrazole ring by a pyridazine ring, in abolishing an intramolecular hydrogen bond between oxygen from amide function and the heterocyclic nitrogen, could lead a better central biodisponibility: in addition, pyridazines are known to have a good central bioavailability.20) Hereafter we report the synthesis and biological evaluation of a series of pyridazine analogues of compound 1 (Fig. 1).To acceed to these compounds, we propose a 3-step synthesis of a series of 3-acetamido-6-arylpyridazines 5a-k.The first strategy we envisaged for the synthesis of 3-N-(2-naphtylacetamido)-6-phenylpyridazine 5b was based on a the sequence shown in route a (Chart 1): treatment of commercially available 3,6-dichloropyridazine 2 with aqueous ammonia 21) to yield the 3-amino-6-chloropyridazine 3, coupling reaction between 3-amino-6-chloropyridazine 3 and 2-naphtylacetic acid in the presence of benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (BOP) 22) produced the 3-N-(2-naphtylacetamido)-3-chloropyridazine 4. Finally we proceeded to a palladium-catalyzed Suzuki cross-coupling reaction between acetamidopyridazine derivative 4 and a commercially available arylboronic acid. However, none of the several literature conditions 23,24) allowed us to obtain 5b with satisfying yields (see Table 1).The key difficulty in preparing compound 5b lies in the cross-coupling reaction at last step. It can be explained by a stacking effect of the naphtyl ring with the pyridazine ring hindering the catalyst approach and by the electron withdrawing effect of amide function on pyridazine ring. To overcome this difficulty, the 3-N-(2-naphtylacetamido)-6-arylpyridazines 5a-k (Table 2) were synthesized as outlined in route b of Chart 1. First a Suzuki cross-coupling reaction of available arylboronic acids with 3-amino-6-chloropyridazine 3 described previously 25) was used to prepare 3-amino-6-arylpyridazine 6 with 12-60% yields. The acetamid...

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ChemInform Abstract: ANTIALLERGIC AGENTS. 3. N‐(1H‐TETRAZOL‐5‐YL)‐2‐PYRIDINECARBOXAMIDES

Honma¹,

Hanamoto²,

Hashiyama³

et al. 1984

Chemischer Informationsdienst

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Antiallergic agents. 3. N-(1H-tetrazol-5-yl)-2-pyridinecarboxamides

Cited by 8 publications

References 0 publications

Photophysical properties of izomeric N-chlorobenzyl substituted (E)-2′ (3′-or 4′)-hydroxy-4-stilbazolium chlorides in alcohols

Photophysical properties of izomeric N-chlorobenzyl substituted (E)-2′ (3′-or 4′)-hydroxy-4-stilbazolium chlorides in alcohols

A Convenient 3-Step Synthesis of 3-Acetamido-6-arylpyridazines Directed to Novel Y5 Receptor Antagonist.

ChemInform Abstract: ANTIALLERGIC AGENTS. 3. N‐(1H‐TETRAZOL‐5‐YL)‐2‐PYRIDINECARBOXAMIDES

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