Developments in antihistamines (H1)

Saxena, Anil Kumar; Saxena, Mridula

doi:10.1007/978-3-0348-7144-0_3

Cited by 4 publications

(5 citation statements)

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“…The majority of clinically useful H 1 antagonists contain a 1,1-diaryl-3-aminopropne moiety where the diaryl group is hypothesized to be a requirement for high affinity at the [ 3 H]mepyramine-labeled H 1 site . In a study of triprolidine analogues, the replacement of one aryl group by hydrogen reduced antihistaminic activity . To test the diaryl requirement at the [ 3 H]-(−)- trans -H 2 -PAT site, compound 19 was synthesized and competition binding for both the [ 3 H]-(−)- trans -H 2 -PAT- and [ 3 H]mepyramine-labeled sites was evaluated (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…(−)- trans -H 2 -PAT incorporates the pharmacophore present in the four prototypical structural classes of histamine H 1 antagonists: the ethylenediamines, the aminoalkyl ethers, the semirigid 1,1-diaryl-3-(alkylamino)propenes, and the 1,1-diaryl-(3-alkylamino)propanes . Functionally, H 1 antagonists have been characterized by their ability to block histamine-induced contraction of guinea pig ileum.…”

Section: Introductionmentioning

confidence: 99%

“…Functionally, H 1 antagonists have been characterized by their ability to block histamine-induced contraction of guinea pig ileum. Structure−activity relationships (SAR) for H 1 antagonists have been reviewed elsewhere. − …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H₁ Receptors

et al. 1999

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A series of 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes (1-phenyl-3-aminotetralins, PATs) previously was found to modulate tyrosine hydroxylase activity and dopamine synthesis in rodent forebrain through interaction with a binding site labeled by [(3)H]-(-)-(1R,3S)-trans-H(2)-PAT. Recently, we have discovered that PATs also bind with high affinity to the [(3)H]mepyramine-labeled H(1) receptor in rat and guinea pig brain. Here, we report the synthesis and biological evaluation of additional PAT analogues in order to identify differences in binding at these two sites. Further molecular modifications involve the pendant phenyl ring as well as quaternary amine compounds. Comparison of about 38 PAT analogues, 10 structurally diverse H(1) ligands, and several other CNS-active compounds revealed no significant differences in affinity at [(3)H]-(-)-trans-H(2)-PAT sites versus [(3)H]mepyramine-labeled H(1) receptors. These results, together with previous autoradiographic brain receptor-mapping studies that indicate similar distribution of [(3)H]-(-)-trans-H(2)-PAT sites and [(3)H]mepyramine-labeled H(1) receptors, suggest that both radioligands label the same histamine H(1) receptors in rodent brain. We also report a revision of our previous comparative molecular field analysis (CoMFA) study of the PAT ligands that yields a highly predictive model for 66 compounds with a cross-validated R(2) (q(2)) value of 0.67. This model will be useful for the prediction of high-affinity ligands at radiolabeled H(1) receptors in mammalian brain.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H₁ Receptors

et al. 1999

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“…In every cell, there are four types of histamine receptors, that is, H1, H2, H3, and H4 [7]. Antihistamines (H1) structure a noteworthy helpful class of medications utilized in the treatment of an assortment of hypersensitive conditions such as rhinitis, urticaria, roughage fever, and even asthma [8,9]. Since their revelation and early improvement during the 1940s, histamine H1 receptor foes (antihistamines) have turned out to be one of the most broadly utilized classes of drugs for unfavorably susceptible issues [10].…”

Section: Introductionmentioning

confidence: 99%

Antihistaminic Activity Models

Gupta

Kanase

Kadam

et al. 2020

Asian J Pharm Clin Res

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Histamine is referred to as common allergic reactions and symptoms. Most of them are compared to histamine intolerance. Some common responses involved with this intolerance may vary but include headaches or migraines, nasal congestion or sinus problems, fatigue, hives, digestive problems, irregular menstrual cycle, nausea, and vomiting. Histamine is derived from a natural amino acid, S-histidine, through the histidine decarboxylase/ aromatic decarboxylase catalysis. Histamine is the compound that the mast cell generates for the immune response. Histamine promotes gastrointestinal secretion and induces capillary dilation, bronchial smooth muscle constriction, and reduced blood pressure. Antihistamines are medicinal products to treat allergic rhinitis and allergies. This includes the in vitro animal model and in-vivo tissue preparation antihistaminic activity. Animal models are significant instruments for understanding the pathological process of human illnesses in experimental medical science. Medicines associated with antihistamine include antiallergy, antivertigo, antimigraine, sedatives, antiemetic, etc. Elderly people are much more likely than youthful people to develop sleepiness from the use of antihistamines. The most common drugs used are cetirizine, levocetirizine, chlorpheniramine, diphenhydramine, loratadine, cimetidine, and fexofenadine. Animal models include histamine-induced bronchoconstriction, passive paw anaphylaxis, milk-induced leukocytosis and eosinophilia, clonidine, and haloperidol-induced catalepsy. While tissue models include isolated goat, and guinea-pig trachea chain preparation, as well as an isolated guinea pig, rat, mice ileum tissue preparation, and the dose-response curve of histamine, were plotted. The focus of the study had been on herbal plants and medicinal products, as they can effectively boost a variety of circumstances without significant adverse side effects. We can assess antihistaminic activity by using plant extracts or any synthetic drug.

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“…Modulation of biological properties is possible by skillful chemical modifications, and variation of substituents and functional groups located in the six-membered benzene rings and the seven-membered heterocyclic ring. This group of compounds includes such important drugs as imipramine (2; a dibenzoazepine with antidepressant activity and a serotonin and norepinephrine reuptake inhibitor) [1], clobenzepam (3; dibenzodiazepine; antihistaminic and anticholinergic) [2], quetiapine (4; dibenzothiazepine; antipsychotic activity; dopamine, serotonin, and adrenergic receptors antagonist) [3], oxcarbazepine (5; dibenzoazepine; anticonvulsant activity; voltage-sensitive sodium channels blocker) [4,5], and nevirapine (6; dipyridodiazepine; anti-HIV; non-nucleoside reverse transcriptase inhibitor) [6]. Additionally, we recently reported [7] the synthesis of structurally related, tricyclic pyrazinebenzodiazepines type 7.…”

Section: Introductionmentioning

confidence: 99%

Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design

et al. 2020

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A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.

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Developments in antihistamines (H1)

Cited by 4 publications

References 203 publications

Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H₁ Receptors

Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H₁ Receptors

Antihistaminic Activity Models

Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design

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Developments in antihistamines (H1)

Cited by 4 publications

References 203 publications

Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H1 Receptors

Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H1 Receptors

Antihistaminic Activity Models

Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design

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Resources

About

Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H₁ Receptors

Synthesis, Evaluation, and Comparative Molecular Field Analysis of 1-Phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as Ligands for Histamine H₁ Receptors