Month: November 2022

Haefele, J. W. published the artcileSynthesis and properties of mercaptans having different degrees of acidity of the sulfhydryl group, Related Products of amides-buliding-blocks, the publication is Proceedings of the Scientific Section of the Toilet Goods Association (1959), 52-9, database is CAplus.

The title compounds were prepared as skin sensitizing materials (Voss, CA 53, 20529e). Mercaptoalkanoic acid amides were made by acylation of amines with the corresponding esters (method 1) or acid chlorides in which the SH group was protected as the Ac derivative (method 2). Another reaction used was the addition of AcSH to olefinic double bonds followed by ammonolysis with NH₄OH. Thus, reaction overnight at room temperature of 180 g. Et thioglycolate with 111 g. methylamine in 375 ml. MeOH yielded 123.3 g. N-methylthioglycolamide, b₅ 91-4°, pK 8.05. Method (1) with increased reaction times and higher temperatures also gave: 73.3% N,N-dimethylthioglycolamide, b₅ 75-8°, pK 8.10; N-ethylthioglycolamide, 63.5%, b₄ 92-3°, pK 8.14 (disulfide m. 101°); N-isopropylthioglycolamide, 6%, b₄ 112° (disulfide m. 94°); N-amylthioglycolamide, 6%, b₄ 131° (disulfide m. 113°); N-hexylthioglycolamide, 70.5%, b₂ 134° (disulfide m. 109°); N-decylthioglycolamide, 72.0%, b_0.5 163° (disulfide m. 118°); N-hydroxyethylthioglycolamide, 96.1% (81.5% purity), pK 8.10 (disulfide m. 86°); N-methoxyethylthioglycolamide, 51.3%, b₂ 115°, pK 8.10; N-(diethylaminoethyl)thioglycolamide, 36.6%, b₂ 122-5°; N,N-bis(2-hydroxyethyl)mercaptoacetamide, 86.0% purity; N-(1,1-dimethylolmethyl)mercaptoacetamide, 86.0% purity; N-(trimethylolmethyl)mercaptoacetamide, 66.0% purity; 2-mercaptopropionamide, 93% purity; thioglycolic hydrazide, 96.5% yield, m. 52-3°, pK 8.05 (disulfide m. 93-4°); 3-mercaptopropionamide, 91% purity; 2-mercaptopropionic hydrazide, 88% purity; 3-mercaptopropionic hydrazide, 96% purity. Acetylthioacetyl chloride (0.2 mole) (from the acid and SOCl₂) and 0.2 mole Et glycinate were added simultaneously at a slow rate to a well stirred suspension of 87 g. CaSO₄ and 100 g. K₂CO₃ in 400 ml. ether at 10-15° to yield after 3 hrs. crystalline Et N-(acetylthioacetyl)glycinate, m. 78.5° (ether); this (0.032 mole) with 0.09 mole aqueous NH₄OH gave 100% conversion to the free thiol. Tetra-O-acetylglucosamine and acetylthioacetyl chloride in CHCl₃ at 0° yielded on precipitation with ligroine 77% N-(acetylthioacetyl)tetra-O-acetylglucosamine, m. 190-1°. Similarly, di-Et N-(acetylthioacetyl)aminomalonate was obtained in 52% yield, m. 91.5° (ether). Mercaptosuccinimide, pK 6.65, was prepared by addition of thiolacetic acid to maleimide in the presence of benzoyl peroxide to give an initial product, m. 91°, hydrolyzed with HCl in MeOH. At 100° in an autoclave, 113 g. morpholine and 78 g. ethylene sulfide gave after 16 hrs. 77.9% N-mercaptoethylmorpholine, b_0.9 72-3°, n²⁰_D 1.5045. Addition of 68.5 g. ethylene sulfide to 81 g. pyrrolidine in 400 ml. dry dioxane followed by stirring and refluxing 6 hrs. yielded 111 g. N-mercaptoethylpyrrolidine, b₂₂ 81°, n²⁰_D 1.5004, on distillation of the mixture In the same way were obtained: N-mercaptoethylpiperidine, b₁₈ 88°, n²⁰_D 1.5011; N-mercaptoethylpyrrolidone (no data); 3-aza-6-oxaheptanethiol, b₃ 57°, n²⁰_D 1.4770; 3-aza-5-(diethylamino)pentanethiol, b_0.3 53°, n²⁰_D 1.4793. N-(S-Acetylthioethyl)pyrrolidinium chloride was prepared in 81.6% yield by reaction of N-mercaptoethylpyrrolidine with AcCl in benzene and precipitation with hexane, m. 152°. The free base, b_0.2 65°, n²⁰_D 1.5011, with excess MeI in ether at room temperature gave after 8 days 85% N-(S-acetylthioethyl)-N-methylpyrrolidinium iodide, m. 159-60° (EtOH). N-Mercaptoethyl-N-methylpyrrolidinium iodide, m. 66-7°, 44.8% yield, pK 7.7, resulted on hydrolysis with MeOH-HCl 6 days at room temperature An analogous route yielded: 92.2% N-(S-acetylthioethyl)morpholinium chloride, m. 204°; N-(S-acetylthioethyl)morpholine, 59.5%, b_1.5 87°, n²⁰_D 1.5050; N-(S-acetylthioethyl)-N-methylmorpholinium iodide, 85.5%, m. 136-9°; N-mercaptoethyl-N-methylmorpholinium iodide, 11.4%, m. 140-3°, pK 7.52. N-Mercaptoethyltrifluoroacetamide, 9.1% yield, b_1.2 57-61°, pK 7.28, was obtained by reaction of NaOMe from 2 g. Na in 50 ml. MeOH with 10.5 g. mercaptoethylamine-HCl and 28 ml. Et trifluoroacetate in a sealed tube at 100° 16 hrs. Mercaptoethylurea was prepared from mercaptoethylamine and 2 moles KOCN with concentrated HCl to give β-ureidoethyl thiocarbamate, ionization constant 0.8 × 10^-9. S-Acetylthioethyl Me sulfone was prepared by refluxing 61 g. Me vinyl sulfone with 48 g. thiolacetic acid and 1 crystal benzoyl peroxide 20 hrs., extracting with 400 ml. EtOH, and distilling the extract to yield 35 g. reddish brown oil, b_0.3 124-38°, crystallized from EtOH to give 16 g. yellow solid, m. 59-60°. Hydrolysis with MeOH-HCl 5 days at room temperature gave 85.9% mercaptoethyl Me sulfone, pale yellow oil, b_0.1 105-7°, n²⁰_D 1.5240, d₂₀ 1.3208, pK 7.92; disulfide m. 152°. Further prepared were hydroxyethyl thioglycolate, b_20-30 86-91°, dimethoxyethyl thiomalate, b_0.5 130-4°, and N-(S-acetylthioethyl)pyrrolidone, m. 37°.

Proceedings of the Scientific Section of the Toilet Goods Association published new progress about 1869-45-0. 1869-45-0 belongs to amides-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is 2,2,2-Trifluoro-N-(2-mercaptoethyl)acetamide, and the molecular formula is C4H6F3NOS, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Smith, N. published the artcileAdenosine receptor subtypes in the airways responses to 5′-adenosine monophosphate inhalation of sensitized guinea-pigs, Recommanded Product: N-(4-Acetylphenyl)-2-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)phenoxy)acetamide, the publication is Clinical and Experimental Allergy (2008), 38(9), 1536-1547, database is CAplus and MEDLINE.

Endogenous adenosine levels are raised in the lungs during asthma attacks. 5′-Adenosine monophosphate (5′-AMP) inhalation in asthmatics causes bronchoconstriction and in sensitized guinea-pigs induces early (EAR) and late asthmatic responses (LAR), airway hyper-reactivity (AHR) and inflammatory cell recruitment to the lungs. The aim of this study was to investigate the roles of A₁, A_2A, A_2B and A₃ adenosine receptors in these responses to inhaled 5′-AMP in sensitized guinea-pigs. Comparisons were made with the effect of dexamethasone treatment on 5′-AMP-induced responses. Functional airways responses to inhaled 5′-AMP (3 and 300 mM) of actively sensitized, conscious guinea-pigs were determined by whole-body plethysmog. following administration of selective adenosine receptor antagonists or their vehicles. AHR to inhaled histamine (1 mM) and inflammatory cell influx in bronchoalveolar lavage fluid were determined 5′-AMP at 3 mM caused an immediate bronchoconstriction (EAR), whereas 300 mM caused bronchodilatation. Both responses were followed at 6 h by a LAR, together with inflammatory cell influx and AHR to histamine. The A_2A receptor antagonist, ZM241385, further enhanced cell influx after 5′-AMP inhalation (3 and 300 mM), and blocked the immediate bronchodilator response to 300 mM 5′-AMP, exposing an EAR. The A_2B receptor antagonist, MRS1706 (in the presence of ZM241385), inhibited the LAR, AHR and cell influx, following inhalation of 5′-AMP (300 mM). The A₃ receptor antagonist, MRS1220, inhibited 5′-AMP-induced inflammatory cell influx. The A₁ receptor antagonist, DPCPX (in the presence of ZM241385), inhibited the EAR following 5′-AMP inhalation (300 mM). Dexamethasone inhibited the LAR, AHR and cell influx following inhalation of 5′-AMP (300 mM). All four adenosine receptor subtypes play various roles in the airways responses to inhaled 5′-AMP in sensitized guinea-pigs.

Clinical and Experimental Allergy published new progress about 264622-53-9. 264622-53-9 belongs to amides-buliding-blocks, auxiliary class GPCR/G Protein,Adenosine Receptor, name is N-(4-Acetylphenyl)-2-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)phenoxy)acetamide, and the molecular formula is C10H10O6, Recommanded Product: N-(4-Acetylphenyl)-2-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)phenoxy)acetamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Anthony, Nahoum G. published the artcileAntimicrobial Lexitropsins Containing Amide, Amidine, and Alkene Linking Groups, Synthetic Route of 64559-06-4, the publication is Journal of Medicinal Chemistry (2007), 50(24), 6116-6125, database is CAplus and MEDLINE.

The synthesis and properties of 80 short minor groove binders, such as I, related to distamycin and the thiazotropsins were described. The design of the compounds was principally predicated upon increased affinity arising from hydrophobic interactions between minor groove binders and DNA. The introduction of hydrophobic aromatic head groups, including quinolyl and benzoyl derivatives, and of alkenes as linkers led to several strongly active antibacterial compounds with MIC for Staphylococcus aureus, both methicillin-sensitive and -resistant strains, in the range of 0.1-5 μg mL^-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 μg mL^-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. Aureus infection for a period of up to six days after a single i.p. dose of 40 mg kg^-1.

Journal of Medicinal Chemistry published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Synthetic Route of 64559-06-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Meresaar, Urve published the artcileHydrolysis of amides. Alkaline and general acid catalyzed alkaline hydrolysis of some substituted acetamides and benzamides, Recommanded Product: N,N-Diethyl-2,2,2-trifluoroacetamide, the publication is Acta Chemica Scandinavica, Series A: Physical and Inorganic Chemistry (1974), 28(7), 715-22, database is CAplus.

AcNH2, trifluoro- and trichloroacetamide, trimethyl- and triethylammonioacetamide cation, benzamide, 4-nitrobenzamide, and N,N-diethyl-, N-cyclohexyl-, and N-benzyltrifluoroacetamide were hydrolyzed at 25 or 45° in alk. solution at ionic strength 1. The pH-rate profiles show that the rate at high pH values is more than first-order in OH- for the trialkylammonioacetamide cations, the benzamides, and N-benzyltrifluoroacetamide, which can be interpreted as OH–catalyzed breakdown of a substrate-OH- intermediate. In accord with a mechanism involving acid catalyzed breakdown of this intermediate to products, the rate of hydrolysis of these amides and of N,N-diethyltrifluoroacetamide and N-cyclohexyltrifluoroacetamide is enhanced by the presence of H phosphate or H carbonate ions. This makes it possible to determine the rate constants for the formation of the tetrahedral intermediates (k1), and the ratios of the rate constants for the uncatalyzed breakdown of the intermediates to products and for their reversion to reactants (k2/k-1). The k2/k-1 values are largely independent of electronic effects in the acyclic part but depend on such effects from substituents in the amine part. The corresponding parameters (k3/k-1) for the OH–catalyzed breakdown of the intermediates were also determined

Acta Chemica Scandinavica, Series A: Physical and Inorganic Chemistry published new progress about 360-92-9. 360-92-9 belongs to amides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain,Amide, name is N,N-Diethyl-2,2,2-trifluoroacetamide, and the molecular formula is C6H10F3NO, Recommanded Product: N,N-Diethyl-2,2,2-trifluoroacetamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Margaroli, Camilla published the artcileDistinct compartmentalization of immune cells and mediators characterizes bullous pemphigoid disease, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Experimental Dermatology (2020), 29(12), 1191-1198, database is CAplus and MEDLINE.

Bullous pemphigoid (BP) is an autoimmune blistering disease characterized by recruitment of leukocytes into skin and release of damaging enzymes, resulting in epidermal detachment and blister formation. To better understand the role of leukotriene B4 (LTB4) and other inflammatory factors in BP pathophysiol., we conducted microscopic and immunohistochem. analyses of preserved skin biopsy sections and conducted flow cytometry and ELISA analyses of matched blood and blister fluid from BP patients. Neutrophils predominated in BP blister fluid, which also contained monocytes/macrophages and T cells, but few to no eosinophils and B cells. In contrast, BP skin histol. showed a different pattern, with abundant neutrophils but eosinophils being the predominant immune cell type. LTB4 pathway and neutrophil activation markers were prevalent in BP skin lesions and strongly associated with perivascular neutrophils. Blister fluid neutrophils, monocytes/macrophages and eosinophils all exhibited increased surface expression of leukotriene A4 hydrolase and neutrophil elastase (P = .002 for both). Blister fluid was also enriched in interleukins (IL)-1α, IL-1β, IL-8, IL-10, IL-18, monocyte colony-stimulating factor (M-CSF) and vascular endothelial growth factor (VEGF). Our findings suggest differential leukocyte recruitment from blood into dermis and from dermis into blister, which correlates with disease activity, and presents potential new treatment opportunities for BP.

Experimental Dermatology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Merzoug, Amina published the artcileMolecular docking study of the acetylcholinesterase inhibition, Category: amides-buliding-blocks, the publication is Current Issues in Pharmacy and Medical Sciences (2021), 34(1), 20-27, database is CAplus.

While Alzheimer disease is the most common form of dementia, acetylcholinesterase is an interesting therapeutic target for the development of new anti-Alzheimer’s disease drugs. In order to discover potential compounds inhibiting this protein target, a mol. docking study of a similar collection of 1-[[2,4-bis[(E)hydroxyiminomethyl] pyridin-1-ium-1-yl]methoxymethyl] pyridin-1-ium-4-carboxamide (HLO) inhibitor from ZINC database using FlexX program was realized. Before performing the mol. docking, FlexX was validated by Root mean square deviation test to determine the reproducibility of the docking program. The strategy undertaken in this study permitted us to propose products 4-[[2-[(Z)-N’-hydroxycarbamimidoyl]-4-pyridyl]methylamino] benzamide and N-[(E)-[1-(4-nitrophenyl)pyrrol-2-yl]methylene amino]isonicotinamide as potential new inhibitors of humane acetylcholinesterase. The two proposed products may act as strong anti-Alzheimer leads compounds

Current Issues in Pharmacy and Medical Sciences published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Canonica, Luigi published the artcileSynthetic analeptics. I. Hydroxybenzoic acid diethylamides, Category: amides-buliding-blocks, the publication is Annali di Chimica (Rome, Italy) (1955), 205-15, database is CAplus.

Of the dialkylamides studied, the best analeptic activity was present in the diethylamides of vanillic acid. Analogs prepared and studied for pharmacol activity were the following benzoic acid diethylamides (substituent given): 4-acetoxy, m. 80-1°; 3-methoxy, b_1.7 132-4°; 2-hydroxy-4-methoxy, m. 121-2°; 2,4-dimethoxy; 2-hydroxy-5-methoxy, m. 103-4°; 3-chloro-4-hydroxy (I); 3-bromo-4-hydroxy (II), m. 158-9°; 3-nitro-4-hydroxy, m. 123-4° (decomposition); 3-chloro-4-acetoxy, m. 89° (crystallized from dilute MeOH); 3-hydroxy, m. 83°; 2-acetoxy, b₁₀ 178-80°; 2-hyhydroxy, m. 104-5°; 3-methoxy-4-hydroxy (III); 3-methoxy-4-acetoxy (IV); 3-ethoxy-4-hydroxy (V), m. 92-3°; 3-ethoxy-4-acetoxy (VI); 4-hydroxy, m. 121.5°; 4-methoxy, m. 42°; 2-acetoxy-4-methoxy, m. 120-1°; 3-bromo-4-acetoxy, m. 94-5° (crystallized from C₆H₆-petr. ether); 3,4,5-trimethoxy, m. 54°, b₅ 203-4°. Piperonylic acid diethylamide, m. 64-5° (from H₂O), and isonicotinic acid diethylamide, b₁₅ 162-4°, were also prepared In general, the acids were converted to acid chlorides with PCl₅ in CS₂ and then to the diethylamide with Et₂NH in C₆H₆. Analeptic activity is given relative to cyclopentamethylenetetrazole. Most active compounds were I to VI in decreasing consecutive order. The presence of a single OH group or OAc increased activity but not significantly. Compounds with a 3-OR group where R = Me or Et were highly active.

Annali di Chimica (Rome, Italy) published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Moral, Alberto published the artcileDevelopment of sol-gel silica-based mixed-mode zwitterionic sorbents for determining drugs in environmental water samples, Synthetic Route of 137862-53-4, the publication is Journal of Chromatography A (2022), 463237, database is CAplus and MEDLINE.

Four novel mixed-mode zwitterionic silica-based functionalized with strong moieties sorbents were synthesized and evaluated through solid-phase extraction (SPE) to determine acidic and basic drugs in environmental water samples. All sorbents had the same functionalization: quaternary amine and sulfonic groups and C18 chains so that hydrophobic and strong cationic exchange (SCX) and strong anionic exchange (SAX) interactions could be exploited, in addition, two of them had carbon microparticles embedded. All sorbents retained both acidic and basic compounds in the preliminary assays but only the basic compounds were retained selectively through ionic exchange interactions when a clean-up step was introduced. The SPE method was therefore optimized to promote the selective retention of the basic compounds, initially with the two best-performing sorbents. After optimization of the SPE protocol, these sorbents were evaluated for the anal. of environmental water samples using liquid chromatog.-tandem mass spectrometry (LC-MS/MS). The method with the best-performing sorbent was then validated with 100 mL of river samples and 50 mL of effluent wastewater samples in terms of apparent recoveries (%Rapp) spiking samples at 50 ng/L (river) and 200 ng/L (river and effluent), matrix effect, linear range, method quantification and detection limits, repeatability, and reproducibility. It should be highlighted that %Rapp ranged from 40 to 85% and matrix effects ranged from -17 to -4% for spiked river samples. When the method was applied to river and effluent wastewater samples, most compounds were found in the range from 24 to 1233 ng/L with detection limits from 1 to 5 ng/L.

Journal of Chromatography A published new progress about 137862-53-4. 137862-53-4 belongs to amides-buliding-blocks, auxiliary class GPCR/G Protein,Angiotensin Receptor, name is (S)-2-(N-((2′-(1H-Tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid, and the molecular formula is C24H29N5O3, Synthetic Route of 137862-53-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Brulet, Jeffrey W. published the artcileLiganding Functional Tyrosine Sites on Proteins Using Sulfur-Triazole Exchange Chemistry, Name: Isonicotinamide, the publication is Journal of the American Chemical Society (2020), 142(18), 8270-8280, database is CAplus and MEDLINE.

Tuning reactivity of sulfur electrophiles is key for advancing click chem. and chem. probe discovery. To date, activation of the sulfur electrophile for protein modification has been ascribed principally to stabilization of a fluoride leaving group (LG) in covalent reactions of sulfonyl fluorides and arylfluorosulfates. We recently introduced sulfur-triazole exchange (SuTEx) chem. to demonstrate the triazole as an effective LG for activating nucleophilic substitution reactions on tyrosine sites of proteins. Here, we probed tunability of SuTEx for fragment-based ligand discovery by modifying the adduct group (AG) and LG with functional groups of differing electron-donating and -withdrawing properties. We discovered the sulfur electrophile is highly sensitive to the position of modification (AG vs. LG), which enabled both coarse and fine adjustments in solution and proteome activity. We applied these reactivity principles to identify a large fraction of tyrosine sites (~30%) on proteins (~44%) that can be liganded across >1500 probe-modified sites quantified by chem. proteomics. Our proteomic studies identified noncatalytic tyrosine and phosphotyrosine sites that can be liganded by SuTEx fragments with site specificity in lysates and live cells to disrupt protein function. Collectively, we describe SuTEx as a versatile covalent chem. with broad applications for chem. proteomics and protein ligand discovery.

Journal of the American Chemical Society published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Name: Isonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Leitão, Andrea Whitehurst Ary published the artcileCelecoxib in the treatment of orofacial pain and discomfort in rats subjected to a dental occlusal interference model., SDS of cas: 169590-42-5, the publication is Acta cirurgica brasileira (2022), 37(5), e370506, database is MEDLINE.

PURPOSE: To evaluate the effect of a selective cyclooxygenase 2 (COX-2) inhibitor on trigeminal ganglion changes and orofacial discomfort/nociception in rats submitted to an experimental model of dental occlusal interference (DOI). METHODS: Female Wistar rats (180-200 g) were divided into five groups: a sham group (without DOI) (n=15); and four experimental groups with DOI treated daily with 0.1 mL/kg saline (DOI+SAL), 8, 16, or 32 mg/kg celecoxib (DOI+cel -8, -16, -32) (n=30/group). The animals were euthanized after one, three, and seven days. The bilateral trigeminal ganglia were analyzed histomorphometrically (neuron cell body area) and immunohistochemically (COX-2, nuclear factor-kappa B [NFkB], and peroxisome proliferator-activated receptor-y [PPARy]). A bilateral nociception assay of the masseter muscle was performed. The number of bites/scratches, weight, and grimace scale scores were determined daily. One-way/two-way analysis of variance (ANOVA)/Bonferroni post hoc tests were used (P < .05, GraphPad Prism 5.0). RESULTS: DOI+SAL showed a reduction in neuron cell body area bilaterally, whereas DOI+cel-32 exhibited a significative increase in neuron cell body area compared with DOI+SAL group (P < 0.05). The ipsilateral (P=0.007 and P=0.039) and contralateral (P < 0.001 and P=0.005) overexpression of COX-2 and NFkB and downregulation of PPARy (P=0.016 and P < 0.001) occurred in DOI+SAL, but DOI+cel-32 reverted this alteration. DOI+SAL showed increase in isplateral (P < 0.001) and contralateral (P < 0.001) nociception, an increased number of bites (P=0.010), scratches (P < 0.001), and grimace scores (P=0.032). In the group of DOI+cel-32, these parameters were reduced. CONCLUSIONS: Celecoxib attenuated DOI-induced transitory nociception/orofacial discomfort resulting from trigeminal COX-2 overexpression.

Acta cirurgica brasileira published new progress about 169590-42-5. 169590-42-5 belongs to amides-buliding-blocks, auxiliary class Sulfamide,Immunology/Inflammation,COX, name is 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide, and the molecular formula is C17H14F3N3O2S, SDS of cas: 169590-42-5.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics