Month: February 2023

New methods for the synthesis of 2-arylpyrroles was written by Kruse, Chris G.;Bouw, Jan P.;Van Hes, Roelof;Van de Kuilen, Aalt;Den Hartog, Jack A. J.. And the article was included in Heterocycles in 1987.COA of Formula: C10H10F3NO2 This article mentions the following:

Two short and efficient synthetic approaches for 2-arylpyrroles I (R = Ph, 4-FC₆H₄, 2,6-F₂C₆H₃, 4-F₃CC₆H₄ etc.) are presented. The key intermediates RCOCH₂CH₂CHO are conveniently obtained from com. available RCOMe or benzoic acid derivatives RCOCl, RCONMeOMe. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7COA of Formula: C10H10F3NO2).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.COA of Formula: C10H10F3NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

An efficient synthesis of 3-cyano-1(3H)-isobenzofuranones was written by Okazaki, Kousuke;Nomura, Keiichi;Yoshii, Eiichi. And the article was included in Synthetic Communications in 1987.Formula: C11H15NO2 This article mentions the following:

Salicylamides I (R¹ = H, OMe, OCH₂OMe; R² = H, OMe, F; R³ = H, OMe; R⁴ = H, OMe, OCH₂OMe, F) were converted to phthalides II in two steps. I were treated with MeSiCN, KCN, and 18-crown-6 to yield cyanohydrin derivatives III, and the latter were kept in HOAc to give II. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Formula: C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Formula: C11H15NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthesis and Investigation of the Antidepressant Properties of Arginine-Vasopressin was written by Borodina, K. V.;Savanets, O. N.;Pustyulga, E. S.;Martinovich, V. P.;Kravchenko, E. V.;Olgomets, L. M.;Golubovich, V. P.. And the article was included in Russian Journal of Bioorganic Chemistry in 2022.Formula: C13H24N2O This article mentions the following:

A search for novel antidepressant analogs of arginine-vasopressin (AVP) by a computer modeling revealed the following peptide analogs of the C-terminal part of AVP: N-Ac-D-Ser-Pro-D-Arg-Gly-NH2, N-Ac-Phe-Pro-Arg-Gly-NH2, and N-Ac-Trp-Pro-Arg-Gly-NH2. Syntheses of the modeled compounds were described in this article. The compounds that could potentially exhibit the antidepressant activity were examined in the forced swimming test. N-Ac-Trp-Pro-Arg-Gly-NH2 (0.1, 1.0, and 10.0 μg/kg) and N-Ac-D-Ser-Pro-D-Arg-Gly-NH2 (1.0 μg/kg) were shown to have the highest similarity to the fluoxetine reference antidepressant according to a number of parameters after the intranasal administration to the Wistar male rats. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Formula: C13H24N2O).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Formula: C13H24N2O

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

N,N’-Dicyclohexyl-N-(phthaloylglycyl)urea was written by Bernes, Sylvain;Hernandez-Linares, Maria Guadalupe. And the article was included in IUCrData in 2021.Computed Properties of C13H24N2O This article mentions the following:

The mol. structure of the title compound {systematic name: 1,3-dicyclohexyl-1-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetyl]urea}, C23H29N3O4, derived from N,N’-dicyclohexylurea, shows that the tertiary N atom substituted by a cyclohexyl and phthaloylglycyl groups adopts a perfectly planar geometry (bond-angle sum = 360.0°). In the same way as for N,N’-dicyclohexylurea, the extended structure of the title compound features N-H···O hydrogen bonds, which generate chains of mols. running in the [001] direction. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Computed Properties of C13H24N2O).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Computed Properties of C13H24N2O

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Design, synthesis and herbicidal activity of novel sulfonylureas containing monosubstituted pyrimidine moiety was written by Pan, Li;Liu, Zhuo;Chen, You-wei;Li, Yong-hong;Li, Zheng-ming. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 2013.Category: amides-buliding-blocks This article mentions the following:

Sulfonylureas, a unique group of herbicides, were extensively applied to controlling a range of weeds in a variety of crops and vegetables. In order to find efficient sulfonylurea herbicides, the title compounds were designed by introducing monosubstituted pyrimidinamines into some well-known sulfonylurea skeletons. A series of sulfonylurea compounds were synthesized and characterized by ¹H NMR and HRMS. Herbicidal activities and IC₅₀ values of the title compounds were determined by Pot plant test and Petri dish test against Brassica napus, Amaranthus retroflexus, Echinochloa crusgalli and Digitaria adscendens. Some compounds exhibited herbicidal activities. Compounds I and II possessed significant inhibition effects against Brassica napus and Amaranthus retroflexus. Further structural modification of novel sulfonylureas containing monosubstituted pyrimidine moiety will be required for improving efficacy against weeds in our laboratory In the experiment, the researchers used many compounds, for example, 2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6Category: amides-buliding-blocks).

2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Category: amides-buliding-blocks

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Screening and evaluation of potential inhibitors against vaccinia virus from 767 approved drugs was written by Wu, Jiajing;Liu, Qiang;Xie, Hui;Chen, Ruifeng;Huang, Weijin;Liang, Chunnan;Xiao, Xinyue;Yu, Yongxin;Wang, Youchun. And the article was included in Journal of Medical Virology in 2019.Related Products of 53902-12-8 This article mentions the following:

The development of therapies for human smallpox is needed due to the increasing concern over the potential use of smallpox virus as a biol. weapon. Here, we report a high-throughput screening for anti-smallpox virus drugs from a 767-small-mol. library, employing two vaccinia virus (VACV) strains containing firefly luciferase (VTT-Fluc and VG9-Fluc) as surrogate viruses. Using an eight-point dose response format assay, 26 compounds of different pharmacol. classes were identified with in vitro anti-VACV activities. Mycophenolate mofetil (MMF) and tranilast (TRA) were detected to possess the highest anti-VACV potency (selectivity index values of >334 and >74, resp.); they could inhibit VTT-Fluc replication in nude mice at 5 days post-infection by 99% (10 mg/kg, P < .01) and 59% (45 mg/kg, P = .01), resp., as indicated by bioluminescent intensity. In conclusion, MMF and TRA are promising anti-smallpox virus candidates for further optimization and repurposing for use in clin. practice. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Related Products of 53902-12-8).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Related Products of 53902-12-8

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

New metal compounds of sulfonamides as fungicides against plant pathogenic fungi was written by Badawi, A. M.;Salama, M. A.;Mahmoud, M. B.. And the article was included in Delta Journal of Science in 1991.Application In Synthesis of N-Isopropylbenzenesulfonamide This article mentions the following:

Copper, zinc, tin, cobalt and mercury complexes of N-iso-Pr benzenesulfonamide were synthesized and tested as fungicides for control of some plant pathogenic fungi. Structure-activity relationships were discussed. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Application In Synthesis of N-Isopropylbenzenesulfonamide).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Application In Synthesis of N-Isopropylbenzenesulfonamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Novel role for tranilast in regulating NLRP3 ubiquitination, vascular inflammation, and atherosclerosis was written by Chen, Suwen;Wang, Yadong;Pan, Yamu;Liu, Yao;Zheng, Shuang;Ding, Ke;Mu, Kaiyu;Yuan, Ye;Li, Zhaoyang;Song, Hongxian;Jin, Ying;Fu, Jian. And the article was included in Journal of the American Heart Association in 2020.Safety of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

Aberrant activation of the NLRP3 (nucleotide-binding oligomerization domain, leucine-rich repeat-containing receptor family pyrin domain-containing 3) inflammasome is thought to play a causative role in atherosclerosis. NLRP3 is kept in an inactive ubiquitinated state to avoid unwanted NLRP3 inflammasome activation. This study aimed to test the hypothesis that pharmacol. manipulating of NLRP3 ubiquitination blunts the assembly and activation of the NLRP3 inflammasome and protects against vascular inflammation and atherosclerosis. Since genetic studies yielded mixed results about the role for this inflammasome in atherosclerosis in low-d. lipoprotein receptor- or apolipoprotein E-deficient mice, this study attempted to clarify the discrepancy with the pharmacol. approach using both models. We provided the first evidence demonstrating that tranilast facilitates NLRP3 ubiquitination. We showed that tranilast restricted NLRP3 oligomerization and inhibited NLRP3 inflammasome assembly. Tranilast markedly suppressed NLRP3 inflammasome activation in low-d. lipoprotein receptor- and apolipoprotein E-deficient macrophages. Through reconstitution of the NLRP3 inflammasome in human embryonic kidney 293T cells, we found that tranilast directly limited NLRP3 inflammasome activation. By adopting different regimens for tranilast treatment of low-d. lipoprotein receptor- and apolipoprotein E-deficient mice, we demonstrated that tranilast blunted the initiation and progression of atherosclerosis. Mice receiving tranilast displayed a significant reduction in atherosclerotic lesion size, concomitant with a pronounced decline in macrophage content and expression of inflammatory mols. in the plaques compared with the control group. Moreover, tranilast treatment of mice substantially hindered the expression and activation of the NLRP3 inflammasome in the atherosclerotic lesions. Tranilast potently enhances NLRP3 ubiquitination, blunts the assembly and activation of the NLRP3 inflammasome, and ameliorates vascular inflammation and atherosclerosis in both low-d. lipoprotein receptor- and apolipoprotein E-deficient mice. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Safety of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Safety of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Condensed pyrimidine systems. XIII. Some amino-substituted derivatives of guanine and 6-thioguanine was written by Elion, Gertrude B.;Lange, William H.;Hitchings, George H.. And the article was included in Journal of the American Chemical Society in 1956.Synthetic Route of C6H7N3O This article mentions the following:

Crude 4,5-diamino-6-hydroxy-2-mercaptopyrimidine (100 g.) refluxed 2 hrs. with 500 cc. 90% HCO₂H, cooled, and filtered, the filter cake pressed dry, suspended in 200 cc. HCONH₂, heated 2 hrs. at 175-85°, cooled, and filtered, and the crude product (100.5 g.) dissolved in 2 l. N NaOH, filtered, and reprecipitated with glacial AcOH gave 90 g. 6-hydroxy-2-mercaptopurine (I). I (42 g.) in 250 cc. 2N NaOH treated slowly with stirring with 31.5 g. Me₂SO₄ at 25-40°, the mixture stirred 1 hr., kept at room temperature overnight, adjusted to pH 5 with glacial AcOH and chilled, and the precipitate washed with cold H₂O and dried at 110° gave 44 g. (98% pure) 6-hydroxy-2-methylthiopurine (II); it did not melt below 300°. II heated with 3-4 molar equivalents aliphatic amine 24 hrs. at 140° (48 hrs. at 160° with aromatic amines) in a sealed tube gave the corresponding 2-(substituted-amino)-6-hydroxypurines (IIa). The mixture with MeNH₂ evaporated to dryness in vacuo, the solid residue dissolved at room temperature in about 5 volumes H₂O and filtered, the filtrate adjusted with AcOH to pH 5, and the precipitate dissolved in 40 volume hot 0.3N HCl and reprecipitated with NH₄OH (pH 6) gave 37% 2-methylamino-6-hydroxypurine (III). A similar run with 14% MeNH₂ in MeOH gave a 65% yield. In the same manner was prepared the EtNH analog of III, in 30% yield from 33% aqueous EtNH₂. The reaction mixture from Me₂NH cooled, diluted with 3 volume MeOH, chilled, and filtered, and the residue recrystallized from 100 parts boiling H₂O gave 50% 2-Me₂N analog of III; in a run with 2 molar equivalents 12% Me₂NH in MeOH the yield was 61%. The mixture from PhNH₂ diluted with 20 volumes 1:1 absolute EtOH-Et₂O precipitated 56% PhNH analog (IV) of III. In the same manner was prepared the p-Cl derivative of IV in 35% yield. The mixture from piperidine (without solvent) diluted with about 4 parts H₂O, filtered, acidified to pH 5 with HCl, and filtered, the filtrate evaporated to dryness in vacuo, the residue treated with 50 parts 1:1 6N HCl-Me₂CO to give the HCl salt of the product, the filter residue extracted several times with 10 parts boiling H₂O, the extract chilled, filtered, and treated in the same manner, and the combined crude solid product recrystallized from 50 parts hot 6N HCl, treated with Darco, and diluted with an equal volume Me₂CO and chilled gave 33% 2-piperidino-6-hydroxypurine (V). A similar run with piperidine in EtOH gave 10% V; a 19% yield of V was obtained in a run with 4 molar equivalents piperidine in 2 molar equivalents concentrated HCl. The appropriate 2-(substituted-amino)-6-hydroxypurine refluxed 3 hrs. with 5 parts freshly pulverized P₂S₅ and 50 parts dry pyridine, the pyridine removed in vacuo, the residue heated 15-20 min. with 40 volume H₂O, cooled, diluted cautiously with an equal volume concentrated NH₄OH, chilled, and filtered, and the filtrate concentrated to a small volume in vacuo, adjusted to pH 5, and chilled gave the corresponding 2-(substituted-amino)-6-mercaptopurine (VI) (substituted-amino group, mole crystal water, and % yield given): MeNH, 0.25, 64; EtNH, 0.5, 45; Me₂N, 1, 52; PhNH, 1.5, 34; piperidino, 0.5, 51. The ultraviolet absorption maximum and min. of the IIa and VI at pH 1 and 11 are tabulated. In the experiment, the researchers used many compounds, for example, 3-Aminopicolinamide (cas: 50608-99-6Synthetic Route of C6H7N3O).

3-Aminopicolinamide (cas: 50608-99-6) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Synthetic Route of C6H7N3O

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A Ruthenium-Catalyzed Cyclization to Dihydrobenzo[c]phenanthridinone from 7-Azabenzonorbornadienes with Aryl Amides was written by Aravindan, Narasingan;Vinayagam, Varathan;Jeganmohan, Masilamani. And the article was included in Organic Letters in 2022.Computed Properties of C9H10FNO2 This article mentions the following:

An efficient ruthenium(II)-catalyzed tandem C-C/C-N bond formation with aryl amides and 7-azabenzonorbornadienes was developed to synthesize cis-fused dihydrobenzo[c]phenanthridinones. The amide group functions as a directing group as well as a leaving group and provided an easy access to the pharmaceutically useful benzo[c]phenanthridine alkaloids such as nitidine and fagaronine analogs. The present methodol. was compatible with various functional groups with respect to azabicyclic alkenes and aromatic amides. The reaction mechanism involving directing-group-assisted C-H activation was proposed and supported by the deuterium labeling studies. In the experiment, the researchers used many compounds, for example, 3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1Computed Properties of C9H10FNO2).

3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Computed Properties of C9H10FNO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics