Month: December 2022

Gelfand, Erwin W. published the artcileImportance of the leukotriene B4-BLT1 and LTB4-BLT2 pathways in asthma, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Seminars in Immunology (2017), 44-51, database is CAplus and MEDLINE.

For several decades, the leukotriene pathways have been implicated as playing a central role in the pathophysiol. of asthma. The presence and elevation of numerous metabolites in the blood, sputum, and bronchoalveolar lavage fluid from asthmatics or exptl. animals adds support to this notion. However, targeting of the leukotriene pathways has had, in general, limited success. The single exception in asthma therapy has been targeting of the cysteinyl leukotriene receptor 1, which clin. has proven effective but only in certain clin. situations. Interference with 5-lipoxygenase has had limited success, in part due to adverse drug effects. The importance of the LTB4-BLT1 pathway in asthma pathogenesis has extensive exptl. support and findings, albeit limited, from clin. samples. The LTB4-BLT1 pathway was shown to be important as a neutrophil chemoattractant. Despite observations made more than two decades ago, the LTB4-BLT1 pathway has only recently been shown to exhibit important activities on subsets of T lymphocytes, both as a chemoattractant and on lymphocyte activation, as well as on dendritic cells, the major antigen presenting cell in the lung. The role of BLT2 in asthma remains unclear. Targeting of components of the LTB4-BLT1 pathway offers innovative therapeutic opportunities especially in patients with asthma that remain uncontrolled despite intensive corticosteroid treatment.

Seminars in Immunology 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

Birkofer, Leonhard published the artcileRegularities in the hydrogenative fission of N-benzyl compounds, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1942), 429-41, database is CAplus.

Because of the value of the preparative method of the catalytic removal of the N-CH₂Ph group, a study has been made of the influence of the residue on the N atom upon catalytic debenzylation. All hydrogenations were carried out at room temperature and atm. pressure in EtOH or AcOH, using PdO or PtO₂ as catalyst. PhCH₂NH₂, (PhCH₂)₂NH and PhCH₂NHMe are unchanged in the presence of PdO. (PhCH₂)₃N in AcOH (PdO) or its HCl salt in H₂O (PdO) gives 97% of (PhCH₂)₂NH.HCl; the amine is not reduced by Na and EtOH. Methylcetylbenzylamine in AcOH (PdO) gives 92% of cetylmethylamine-HCl and lauryldibenzylamine gives laurylmethylamine. Dodecyldibenzylamine in AcOH (PtO₂) gives 84% of dodecylhexahydrobenzylamine-HCl, m. 218°. (PhCH₂)₂NNH₂ in absolute EtOH (PdO) yields 88% of PhCH₂NHNH₂; tetrabenzyltetrazene [(PhCH₂)₂NN:]₂ gives (PhCH₂)₂NH. (PhCH₂)₃MeNOH with PdO in EtOH readily yields PhCH₂NHMe (flavianate, m. 190°; picrolonate, m. 210°), whereas (PhCH₂)₃MeNI is not reduced. PhCH₂NPhMe₂Cl gives 90% of cyclohexyldimethylamine. 2-Benzyldihydroisoindole in EtOH (PdO) yields 75% of 1,3-dihydroisoindole, b₃ 100°. 1,4-Dibenzylpiperazine in AcOH (PdO) gives 92% of piperazine diacetate, m. 234°. α-Monobenzylaminotetrazole gives aminotetrazole. PhCH₂NH₂ (1 mol.) in AcOEt is treated with a concentrated aqueous solution of 4 mols. of KCN and then dropwise with 1.1 mols. of Br in AcOEt at 5-10°, and the AcOEt solution shaken with 30% NaOH; the alkali removes the benzylcyanamide, which is polymerized to tribenzylisomelamine (1,3,5-tribenzyl-2,4,6-triimino-1,3,5-triazine) (I), m. 129-30°; short heating with HCl gives NH₃; with H and PdO in EtOH this yields melamine. The elimination of PhCH₂ from 2-imino-1-benzyl-1,2-dihydropyridine is slow and incomplete and is accompanied by nuclear hydrogenation, the products being 2-amino-3,4,5,6-tetrahydropyridine and 2-imino-1-benzylpiperidine (picrate, m. 106°). 2-Benzylaminopyridine does not lose PhCH₂ but is hydrogenated to 2-benzylamino-3,4,5,6-tetrahydropyridine, m. 40-1° (picrate, yellow, m. 131°; picrolonate, yellow, m. 199°). Aromatic rings, CO₂H and CN groups activate the compounds so that PhCH₂ is removed from a sec-N atom. PhNHCH₂Ph in EtOH (PdO) gives 97.5% of PhNH₂ and PhMe, whereas PtO₂ gives mainly cyclohexylhexahydrobenzylamine and small amounts of cyclohexylamine and hexahydrotoluene. PhN(CH₂Ph)₂ with PdO in EtOH gives 89% of PhNH₂ and PhMe. 2-(Dibenzylamino)naphthalene in AcOH (PdO) gives 88% of 2-C₁₀H₇NH₂ and PhMe. ClCH₂CO₂H (9 g.) and 40 g. (PhCH₂)₂NH in 20 cc. dioxane, heated 5 h. at 120°, give 82% of N,N-dibenzylglycocoll, m. 200°; Me ester, m. 41°; hydrogenation in AcOH (PdO) or in EtOH (PdO) gives NH₂CO₂H (95%) or its Me ester (96%). (PhCH₂)₂NCN yields NCNH₂ or I because of polymerization of PhCH₂NHCN if hydrogenation is interrupted before it is complete. (CONHCH₂Ph)₂ and N,N-dibenzylurethane, b₂ 169°, b₄ 181° (82% yield), are stable toward H.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Recommanded Product: N,N-Dibenzylcyanamide.

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

Bianchi, Maria C. published the artcileSome Aliphatic Cyanoacetylamines, SDS of cas: 15029-36-4, the publication is Atti accad. sci. Torino (1913), 654-9, database is CAplus.

5 cc. CNCH₂CO₂Et in 35 cc. Et₂O + 20 cc. absolute alc. after a passage of an excess of NH₃ gave 3 g. NCCH₂CONH₂, crystals from MeOH, m. 124-5°. 7 g. CNCH₂CO₂Et in 25 cc. Et₂O + 17 cc. absolute alc. and 25 cc. of 20% MeNH₂ gave 5 g. of cyanoacetmethylamide, CNCH₂CONHMe, m. 104-5°, decompose with KOH, neutralized with HCl its solution becomes yellow. Similarly, the ethylamide, colorless prisms from EtOH, m. 74-50. CNCH₂CO₂Et (2 mol.) + propylenediamine (1 mol.) gives dicyanoacetopropylenediamide, (CNCH₂CONH)₂C₂H₆, m. 161-2°, with KMnO₄ gives HCN and the corresponding propyleneoxamic acid. Similarly the trimethylenediamide, CH₂(CH₂NHCOCH₂CN)₂, m. 163-5°, decompose 200-10°, giving NH₃, gives a neutral H₂O solution, gives HCN and the corresponding oxamic acid with KMnO₄.

Atti accad. sci. Torino published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C5H8N2O, SDS of cas: 15029-36-4.

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

Bany, T. published the artcileChloroalkylamines, drugs paralyzing the endings of the sympathetic system, Name: N,N-Dibenzylcyanamide, the publication is Acta Poloniae Pharmaceutica (1955), 223-32, database is CAplus.

Derivatives of N,N-dibenzyl-β-chloroethylamine (Dibenamine) containing Br, I, or F and substituents other than benzyl are described as having possible paralyzing properties of the sympathetic system and action against malignant growth. FCH₂CH₂OH (I), b. 100-2°, was prepared in about 40% yield by adding with stirring 80 g. ClCH₂CH₂OH to a mixture of 87 g. KF (dried at 170°) and 110 g. HOCH₂CH₂OH heated at 210° at such a rate that a fraction b. 95-105° is distilled from the mixture, treating the distillate with 2 g. NaF, filtering and redistilling. FCH₂CH₂Cl (II), b₇₅₀ 57°, d₂₃ 1.1764, n_D²³ 1.3842 was obtained in 30% yield by adding 145 g. SOCl₂ to 60 g. I, refluxing 3 hrs. on a water bath, adding water, washing the resulting oil with NaHCO₃ and water, drying over CaCl₂ and distilling FCH₂CH₂Br (III), b₇₄₃ 72°, was obtained in a 23.7% yield by heating 7 g. I with 65 g. PBr₅ 3 hrs., washing the oil with water and Na₂CO₃, taking up in ether, drying and distilling (PhCH₂)₂NH.HCl (IV), not m. below 350°, was obtained by refluxing a mixture of 10 g. Na₂NCN, 45 g. water, 55 g. EtOH, and 25.2 g. PhCH₂Cl 36 hrs., distilling water and EtOH, crystallizing from petr. ether the resulting (PhCH₂)₂NCN, m. 112°, boiling it with 16 g. H₂SO₄ and 48 g. water 6 hrs., adding 26 g. NaOH in 48 g. water, steam distilling the amine, extracting the distillate with ether, treating the extract with HCl and filtering the precipitate (PhCH₂)₂NCH₂CH₂F.HCl (V), m. 248-50°, was prepared in 53% yield by heating 8 g. (PhCH₂)₂NH and 4 g. II in a sealed tube at 120-60° 24 hrs. and crystallizing from EtOH. (PhCH₂)₂NCH₂CH₂Br.HBr (VI), m. 181-2°, was obtained in 68% yield by adding HBr to 5 g. (PhCH₂)₂NCH₂CH₂OH (VII), filtering and drying the VII.HBr (m. 164°), heating it on a water bath 2 hrs. with 8.4 g. PBr₃ and 20 ml. CHCl₃, distilling the CHCl₃, adding EtOH, filtering the mixture, distilling the EtOH, and crystallizing from EtOH. Refluxing 6 g. VI and 5 g. NaI.2H₂O in 100 ml. AcOMe 2 hrs., evaporating to 0.5 volume, and cooling gave 7.2 g. (PhCH₂)₂NCH₂CH₂I.HI, m. 173-4° (from EtOH). (PhCH₂CH₂)₂NCH₂CH₂Cl.HCl (VIII), m. 153-4°, was obtained in 86.2% yield by refluxing 4 g. (PhCH₂CH₂)₂NCH₂CH₂OH in 20 ml. CHCl₃ with 2.5 g. SOCl₂ 4 hrs., removing CHCl₃, crystallizing the residue from EtOH-Et₂O and recrystallizing from AcOMe. (PhCH₂CH₂)₂NCH₂CH₂I.HI, m. 159-60°, was prepared in 85.7% yield by refluxing 1 g. VIII and 1.5 g. NaI.2H₂O in 25 ml. AcOMe 2 hrs., filtering off the precipitate, distilling the filtrate, taking up the residue in CHCl₃, filtering again, concentrating the filtrate and recrystallizing the solid from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂Cl.HCl (IX), m. 185-6°, was prepared in 89.6% yield by refluxing 5 g. (α-C₁₀H₇CH₂)₂NCH₂CH₂OH and 2.7 g. SOCl₂ in 25 ml. CHCl₃ 4 hrs., distilling the CHCl₃, cooling, filtering off the precipitate, and crystallizing from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂Br.HBr, m. 199-200°, was obtained in 82.5% yield by heating a solution of 1 g. IX in 5 ml. absolute EtOH with 1.2 g. CaBr₂.6H₂O in a min. quantity of absolute EtOH 6 hrs., cooling and recrystallizing from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂I.HI, m. 181-2°, was obtained in 82.7% yield by heating 2 g. IX and 1.55 g. NaI.2H₂O in EtOH 8 hrs., cooling, filtering off the NaCl, concentrating the filtrate, and recrystallizing from MeOH. The piperidine derivative, C₅H₁₀NCH₂CH₂Cl.HCl (X), m. 234°, was obtained in 28.4% yield by heating on a water bath 13 g. C₅H₁₀NH with 12 g. ClCH₂CH₂OH 6 hrs., adding 50 ml. CHCl₃ and 23 g. SOCl₂, refluxing an addnl. 3 hrs., distilling the CHCl₃ and crystallizing from absolute EtOH. C₅H₁₀NCH₂CH₂Br.HBr, m. 219-20°, was obtained in 5.6% yield by refluxing 2 g. X and 2 g. CaBr₂.6H₂O in EtOH 6 hrs., distilling EtOH and crystallizing from AcOMe. C₅H₁₀NCH₂CH₂I.HI, m. 212-13°, was prepared in 5% yield by refluxing 2 g. X and 3 g. NaI.2H₂O in EtOH 6 hrs. and crystallizing from MeOH. C₅H₁₀NCH₂CH₂F.HCl (not m. below 350°) was prepared by heating 5 g. C₅H₁₀NH and 5 g. II 12 hrs. in a sealed tube at 140-60° and crystallizing from dilute EtOH.

Acta Poloniae Pharmaceutica published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Name: N,N-Dibenzylcyanamide.

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

Ball, Nicholas D. published the artcileSulfondiimidamides unlocked as new S(VI) hubs for synthesis and drug discovery, Recommanded Product: 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide, the publication is Chem (2022), 8(4), 907-909, database is CAplus.

A review. Despite their promise as drug targets, access to nitrogen-rich S(VI) compounds has been a significant synthetic challenge. In this issue of Chem, Zhang and Willis explore a new class of S(VI) compounds-sulfondiimidamides-providing robust strategies toward their synthesis, derivation, and promise as new sulfonamide bioisosteres.

Chem 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, Recommanded Product: 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide.

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

Bald, Edward published the artcileThe synthetic utility of 2-halopyridinium salts. Preparation of pyridinemonocarboxylic esters and amides under mild conditions, Related Products of amides-buliding-blocks, the publication is Chemica Scripta (1979), 13(1), 47, database is CAplus.

The equimolar reaction of pyridinemonocarboxylic acids with alcs. or amines and 2-chloro-1-methylpyridinium iodide in the presence of 2 M amounts of Et₃N gave the corresponding pyridinemonocarboxylic esters or amides in good yields.

Chemica Scripta 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, Related Products of amides-buliding-blocks.

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

Al-Etaibi, Alya M. published the artcileSynthesis and antimicrobial activity of some disperse dyes derived from pyridones, Related Products of amides-buliding-blocks, the publication is International Journal of ChemTech Research (2019), 12(5), 129-133, database is CAplus.

Pyridone derivatives 4a,b are prepared by reacting N-alkyl-2-cyanoacetamide 1a,b with Me propionylacetate. Compounds 4a,b are coupled with aromatic diazonium salts to produce the corresponding new azo disperse dyes 6a,b. The antimicrobial activity of the synthesized azo disperse dyes are evaluated.

International Journal of ChemTech Research published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C5H8N2O, Related Products of amides-buliding-blocks.

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

Abu-Hashem, Ameen Ali published the artcileSynthesis of new pyrazoles, oxadiazoles, triazoles, pyrrolotriazines, and pyrrolotriazepines as potential cytotoxic agents, Safety of 2-Chloroacetamide, the publication is Journal of Heterocyclic Chemistry (2021), 58(3), 805-821, database is CAplus.

The 4-oxo-4-phenylbutanehydrazide reacted with many active methylene reagents such as acetylacetone, diethylmalonate, ethylacetoacetate, ethylcyanoacetate, benzoyl-acetonitrile, and malononitrile under neat conditions to afford the corresponding pyrazoles e.g., I, also, treatment of 4-oxo-4-phenylbutanehydrazide with electrophilic reagents as triethylorthoformate, dimethylformamide-dimethylacetal, acetic anhydride, and carbon disulfide to give 1,3,4-oxadiazoles e.g., II and N’-acetyl-4-oxo-4-phenylbutanehydrazide. Reaction of 4-oxo-4-phenylbutanehydrazide with potassium thiocyanate gave 1-phenyl-3-(5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)propan-1-one. Similarly, treatment of 4-oxo-4-phenylbutanehydrazide with chloroacetamide gave 3-(3-oxo-3-phenylpropyl)-1,6-dihydro-1,2,4-triazin-5(2H)-one. The 6-phenyl-3,4-dihydropyrrolo[1,2-b][1,2,4]triazin-2(8H)-one was obtained by cyclization of 3-(3-oxo-3-phenylpropyl)-1,6-dihydro-1,2,4-triazin-5(2H)-one. Also, 4-oxo-4-phenylbutanehydrazide was utilized as a starting material for the synthesis of new Schiff bases as N’-(4-sub-benzylidene)-phenylbutane-hydrazides C₆H₅C(O)(CH₂)₂C(O)NHN=CHAr (Ar = Ph, 4-chlorophenyl, 4-methoxyphenyl), which are used as an initiative to prepare new compounds such as 1,2,4-triazepinones III, pyrrolotriazepinones IV, 1,2,4-triazines V, and pyrrolotriazines VI by reaction of N’-(4-sub-benzylidene)-phenylbutane-hydrazides with each chloroacetamide or formamide. The prepared compounds were tested for their in vitro antitumor activities. The compounds III, IVand VI displayed activity against several types of cancer cell lines.

Journal of Heterocyclic Chemistry published new progress about 79-07-2. 79-07-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Aliphatic hydrocarbon chain,Amide,Inhibitor, name is 2-Chloroacetamide, and the molecular formula is C2H4ClNO, Safety of 2-Chloroacetamide.

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

Dubovtsev, Alexey Yu. published the artcileAcid-catalyzed [2+2+2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines, Quality Control of 2451-91-4, the publication is Organic & Biomolecular Chemistry (2021), 19(20), 4577-4584, database is CAplus and MEDLINE.

Triflic acid (10 mol%) catalyzes the highly regioselective [2+2+2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed d. functional theory calculations verified a particular role of H⁺, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition

Organic & Biomolecular Chemistry published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Quality Control of 2451-91-4.

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

Yang, Peiying published the artcileCelecoxib colorectal bioavailability and chemopreventive response in patients with familial adenomatous polyposis, Recommanded Product: 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide, the publication is Cancer Prevention Research (2022), 15(4), 217-223, database is CAplus and MEDLINE.

Why celecoxib exerts chemopreventive activity in only some familial adenomatous polyposis (FAP) patients remains poorly understood. We conducted a phase II clin. study to identify potential predictive biomarkers for celecoxib chemopreventive activity in FAP. Twenty-seven patients with FAP completed a 6-mo oral course of 400 mg of celecoxib twice a day; they underwent colonoscopies before and after celecoxib treatment to assess colorectal polyp tumor burden and to obtain normal and polyp colorectal biopsies to measure celecoxib, 13-S-hydroxyoctadecadienoic acid (13-HODE), 15-HETE, 12-HETE, and LTB4 levels by LC/MS-MS. Celecoxib levels in sera from those patients were also measured before treatment and after 2, 4, and 6 mo of treatment. Nineteen of the 27 patients experienced a response to celecoxib, with a = 28% reduction of colonic polyp burden on the basis of a reproducible quant. assessment of colonoscopy results. Celecoxib levels were significantly lower in polyp tissues than in normal colorectal tissues. Celecoxib levels in sera and normal colorectal tissues were correlated in patients who experienced a response to celecoxib but not in those who did not. Among the measured lipoxygenase products, only 13-HODE levels were significantly lower in polyp tissues than in normal tissues. Our findings demonstrate the differential bioavailability of celecoxib between normal and polyp tissues and its potential effects on clin. response in patients with FAP.

Cancer Prevention Research 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 C8H6F3NO, Recommanded Product: 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide.

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