Category: 54166-95-9

Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A₄ hydrolase aminopeptidase inhibitors was written by Zhang, Fan;Wu, Dang;Wang, Gao-Lei;Hou, Shuang;Ping, Ou-Yang;Huang, Jin;Xu, Xiao-Yong. And the article was included in Chinese Chemical Letters in 2017.Formula: C7H7ClN2O This article mentions the following:

A series of novel 1,2,3-benzotriazin-4-one derivatives I [R = H, 6-O₂N, 7-Cl, etc.; X = (CH₂)_n; n = 0, 1, 2, 3, 4] were designed, synthesized and their inhibitory activities against leukotriene A4 hydrolase aminopeptidase in-vitro were evaluated. Many compounds showed moderate to good activities at the concentration of 10 μmol/L. Among them, compound I [R = 7-Cl; X = (CH₂)₄ (II)] exhibited the highest inhibitory activity up to 80.6% with an IC₅₀ of 1.30 ± 0.20 μmol/L. The compound II was also tested for the proliferation inhibitory activities in THP1 human AML cell line and its binding model with LTA4H enzyme by mol. docking was studied. It indicated that 1,2,3-benzotriazin-4-one was a promising scaffold for further study. The relationship between structure and inhibitory activity was also preliminarily discussed. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Formula: C7H7ClN2O).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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. 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.Formula: C7H7ClN2O

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

Site-Selective C-H Amidation of 2-Aryl Quinazolinones Using Nitrene Surrogates was written by Kim, Saegun;Jeoung, Daeun;Kim, Kunyoung;Lee, Seok Beom;Lee, Suk Hun;Park, Min Seo;Ghosh, Prithwish;Mishra, Neeraj Kumar;Hong, Suckchang;Kim, In Su. And the article was included in European Journal of Organic Chemistry in 2020.Safety of 6-Chloro-2-aminobenzamide This article mentions the following:

The site-selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)-catalyzed C-H amidation of 2-aryl quinazolin-4(3H)-ones with a range of nitrene surrogates including dioxazolones, organic azides, and N-methoxyamides. Complete site-selectivity and functional group tolerance are observed Notably, the large-scale reaction and late-stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Safety of 6-Chloro-2-aminobenzamide).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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. 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.Safety of 6-Chloro-2-aminobenzamide

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

The synthesis of proximal-benzolumazine, proximal-benzoxanthine, proximal-benzotheophylline and proximal-benzocaffeine was written by Schneller, Stewart W.;Christ, William J.. And the article was included in Journal of Heterocyclic Chemistry in 1981.Application of 54166-95-9 This article mentions the following:

Title compounds I and II (R = R¹ = H; R = R¹ = Me; R = Me, R¹ = H) were prepared by commencing with 2,6-Cl(H₂H)C₆H₃CONH₂ and proceeding via a variety of 5,6-disubstituted 2,4(1H,3H)-quinazolinediones. Methylation of II (R = Me, R¹ = H) gave III and II (R = R¹ = Me) in a ratio of 4:1. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Application of 54166-95-9).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. 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.Application of 54166-95-9

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

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole against Meloidogyne incognita was written by Zhang, Ruifeng;Guo, Wei;Wang, Gaolei;Chen, Xiulei;Li, Zhong;Xu, Xiaoyong. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.Category: amides-buliding-blocks This article mentions the following:

Based on the characteristic of benzo[d][1,2,3]thiadiazole to induce the systemic acquired resistance and improve the immunity of plants, benzo[d][1,2,3]thiadiazole was introduced into 1,2,3-benzotriazin-4-one, thirty-one novel 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole were designed and synthesized. Nematicidal activity showed that most of the synthesized compounds exhibited great inhibitory activity in vivo against Meloidogyne incognita at 20 mg/L. Among 31 tested compounds, I and II showed an excellent nematicidal activity with the inhibition rate of 50.4% and 53.1% at the concentration of 1.0 mg/L, resp. The influence of substituent type and position was studied. The relation between structure and activity was also preliminary analyzed. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Category: amides-buliding-blocks).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Category: amides-buliding-blocks

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

The synthesis of proximal-benzoguanine and a simplified synthesis of proximal-benzohypoxanthine was written by Schneller, Stewart W.;Ibay, Augusto C.. And the article was included in Journal of Organic Chemistry in 1986.Formula: C7H7ClN2O This article mentions the following:

7-Aminoimidazo[4,5-f]quinazolin-9(8H)-one (proximal-benzoguanine I, R = NH₂) was prepared in five steps from 2-amino-6-chlorobenzamide. Methylation of I (R = NH₂) gave exclusively 7-amino-3-methylimidazo[4,5-f]quinazolin-9(8H)-one(II). (proximal-Benzohypoxanthine I(R = H) was available directly from 3-amino-2,6-dinitrobenzonitrile in a more efficient route than the one previously reported in the literature. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Formula: C7H7ClN2O).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Formula: C7H7ClN2O

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

In-Water Synthesis of Quinazolinones from 1,1-Dichloro-2-nitroethene and Anthranilamides was written by Zhu, Fengjuan;Song, Runjiang;Li, Shen;Shao, Xusheng. And the article was included in Synlett in 2016.Recommanded Product: 6-Chloro-2-aminobenzamide This article mentions the following:

An efficient synthetic methodol. was developed for direct formation of quinazolinones with 2-nitromethyl substituent via 1,1-dichloro-2-nitroethene and anthranilamides. This strategy provides an alternative for quinazolinones construction with merits of proceeding in water, easy purification, and no addition of catalysts. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Recommanded Product: 6-Chloro-2-aminobenzamide).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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. 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.Recommanded Product: 6-Chloro-2-aminobenzamide

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

Novel and efficient one-pot tandem synthesis of tryptanthrin derivatives for biological activity was written by Rama Krishnam Raju, Addada;Venkata Reddy, Regalla;Venkateswara Rao, Anna. And the article was included in International Journal of Pharma Research and Health Sciences in 2018.Related Products of 54166-95-9 This article mentions the following:

The derivatives of tryptanthrins I [R = H, 1-Me, 2-Br, etc; R¹ = H, 8-OMe, 8-Br, etc.] were prepared from three schemes. Those tryptanthrin derivatives I were characterized by NMR study. Treatment of an equimolar mixture of anthranilamides and 2-bromoacetophenones afforded indolo[2,1-b]-quinazoline-6,12-diones (tryptanthrin). In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Related Products of 54166-95-9).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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 can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Related Products of 54166-95-9

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

Herbicides. IV. The synthesis of 2,6-dichlorobenzonitrile was written by Koopman, H.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1961.Recommanded Product: 6-Chloro-2-aminobenzamide This article mentions the following:

Four new methods were described for the synthesis of 2,6-dichlorobenzonitrile (I). Method A: 2,6-Dichloroaniline was diazotized and the diazonium compound converted by the (Sandmeyer) reaction into 75% I when the Sandmeyer catalyst was buffered with NaHCO₃. Method B: 2,3-Dichloronitrobenzene was treated with CuCN and pyridine to give 75% 2-chloro-6-nitrobenzonitrile, 120-2° (MeOH), which was reduced with iron in concentrated HCl-MeOH to give 89% 2-amino-6-chloro-benzonitrile, m. 136-8° (benzene). Sandmeyer reaction there gave 79% I. Iron reduction and partial saponification 2-chloro-6-nitrobenzonitrile gave 41% 2-amino-6-chlorobenzamide, m. 130-1°. Method C: 2,6-dichlorobenzaldehyde and HONHSO₃Na gave 99% anti-2,6-dichlorobenzaldoxime, m. 175-6° (benzene), which was dehydrated by refluxing with Ac₂O to 95% I. To prove the anti structure both the anti- and the syn-2,6-dichlorobenzaldoxime acetate were prepared, m. 80-5° and 43-6°, resp. Method D: By vapor phase reaction, 2,6-dichlorotoluene, excess ammonia, air, and N at 360° on Al₂O₃V₂O₅-catalyst gave 50% I. I strongly inhibited the germination of seeds and the growth of young plants. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Recommanded Product: 6-Chloro-2-aminobenzamide).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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.Recommanded Product: 6-Chloro-2-aminobenzamide

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

Au^I-Catalyzed Direct Hydroamination/Hydroarylation and Double Hydroamination of Terminal Alkynes was written by Patil, Nitin T.;Lakshmi, Pediredla G. V. V.;Singh, Vipender. And the article was included in European Journal of Organic Chemistry in 2010.Reference of 54166-95-9 This article mentions the following:

An efficient method for formal Markownikoff hydroamination/hydroarylation and double hydroamination of terminal alkynes has been developed. For example, treatment of terminal alkynes with amino aromatics or diamines in the presence of 2-5 mol-% of Ph₃PAuNTf₂ in toluene at 100 °C gave the corresponding products in excellent yields. The method was shown to be applicable to a broad range of substrates and, more importantly, unlike our previously reported method, a tethered hydroxy group in the alkyne is not necessary. The mechanism of the reaction is also discussed. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Reference of 54166-95-9).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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 can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Reference of 54166-95-9

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

Design, synthesis and biological activities of 2,3-dihydroquinazolin-4(1H)-one derivatives as TRPM2 inhibitors was written by Zhang, Han;Liu, Huan;Luo, Xiao;Wang, Yuxi;Liu, Yuan;Jin, Hongwei;Liu, Zhenming;Yang, Wei;Yu, Peilin;Zhang, Liangren;Zhang, Lihe. And the article was included in European Journal of Medicinal Chemistry in 2018.Electric Literature of C7H7ClN2O This article mentions the following:

In this study, a series of novel 2,3-dihydroquinazolin-4(1H)-one derivatives, e.g. I was subsequently synthesized and characterized. Their inhibitory activity against the TRPM2 channel was evaluated by calcium imaging and electrophysiol. approaches. Some of the compounds exhibited significant inhibitory activity, especially 6-bromo-8-methyl-2-[3-(2-naphthyl)-1H-pyrazol-4-yl]-2,3-dihydro-1H-quinazolin-4-one which showed an IC₅₀ of 3.7μM against TRPM2 and did not affect the TRPM8 channel. The summarized structure-activity relationship (SAR) provided valuable insights for further development of specific TRPM2 targeted inhibitors. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Electric Literature of C7H7ClN2O).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) 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.Electric Literature of C7H7ClN2O

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