Tag: 100-200

Discovery of penipanoid C-inspired 2-(3,4,5-trimethoxybenzoyl)quinazolin-4(3H)-one derivatives as potential anticancer agents by inhibiting cell proliferation and inducing apoptosis in hepatocellular carcinoma cells was written by Wang, Chao-Jie;Guo, Xinxin;Zhai, Rui-Qin;Sun, Changning;Xiao, Guokai;Chen, Jin;Wei, Mei-Yan;Shao, Chang-Lun;Gu, Yuchao. And the article was included in European Journal of Medicinal Chemistry in 2021.Application of 119023-25-5 This article mentions the following:

Hepatocellular carcinoma (HCC) is the most common form of liver cancer and the fourth leading cause of cancer-related death worldwide. First-line drugs such as sorafenib provide only a modest benefit to HCC patients. In this study, the gram-scale synthesis of 2-benzoylquinazolin-4(3H)-one skeleton was achieved successfully via the I₂/DMSO catalytic system. A series of penipanoid C-inspired 2-(3,4,5-trimethoxybenzoyl)quinazolin-4(3H)-one derivatives was synthesized and evaluated for their cytotoxic activities against four cancer cell lines, HepG2, Bel-7402, A549, and U251. Among these compounds, I was the most effective one with IC₅₀ values of 1.22μM and 1.71μM against HepG2 and Bel-7402 cells, resp. Mechanistic studies showed that I inhibited hepatocellular carcinoma cell proliferation via arresting cell cycle. Addnl., I induced HepG2 cells apoptosis by inducing reactive oxygen species production and elevating the expression of apoptosis-related proteins. More importantly, I displayed significant in vivo anticancer effects in the HepG2 xenograft models. This suggests that I is a promising lead compound with the potential to be developed as a chemotherapy agent for hepatocellular carcinoma. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5Application of 119023-25-5).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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 can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application of 119023-25-5

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

Enantioselective synthesis of dihydropyrans. Catalysis of hetero Diels-Alder reactions by bis(oxazoline) copper(II) complexes was written by Evans, David A.;Johnson, Jeffrey S.;Olhava, Edward J.. And the article was included in Journal of the American Chemical Society in 2000.Synthetic Route of C6H12N2O4 This article mentions the following:

C₂-sym. bis(oxazoline)-Cu(II) complexes catalyze the inverse electron demand hetero Diels-Alder reaction of α,β-unsaturated carbonyl compounds (heterodiene), e.g., (MeO)₂P(O)COCR¹:CR²R³ (R¹, R³ = H, Me, R² = Me, Ph, CHMe₂, EtO, Et), with electron-rich olefins (heterodienophile), e.g., EtOCH:CH₂, in high diastereo- and enantioselectivity. α,β-Unsaturated acyl phosphonates and β,γ-unsaturated α-keto esters and amides are effective heterodienes, while enol ethers and sulfides function as heterodienophiles. A range of substitution patterns is possible on the heterodiene: terminal alkyl, aryl, alkoxy, and thioether substituents are all tolerated. The enantioselective synthesis of dihydropyrans such as I by this method has been shown to be straightforward: cycloadditions may be conducted with as little as 0.2 mol % of the chiral catalyst and are readily run on multigram scale. The reactions exhibit a favorable temperature-enantioselectivity profile, with selectivities exceeding 90% even at room temperature A simple reaction protocol that employs a solid air-stable catalyst, convenient reaction temperatures, and low catalyst loadings is described. The utility of the derived cycloadducts in the preparation of chiral building blocks is demonstrated. Models for asym. induction are discussed considering product stereochem., X-ray crystallog. data for the solid catalysts, and mechanistic studies. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Synthetic Route of C6H12N2O4).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. 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.Synthetic Route of C6H12N2O4

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

An Efficient Approach to Azolyl-Substituted Steroids through Copper-Catalyzed Ullmann C-N Coupling was written by Kotovshchikov, Yury N.;Latyshev, Gennadij V.;Lukashev, Nikolay V.;Beletskaya, Irina P.. And the article was included in European Journal of Organic Chemistry in 2013.Computed Properties of C11H15NO2 This article mentions the following:

Ullmann-type C-N coupling of vinyliodides and nitrogen heterocycles has been shown to be a straightforward and highly efficient approach to azolyl-substituted steroids, e.g., I [R = H, OMe, Br] and II. The amination reaction proved sensitive to steric effects exerted by the substituents in both iodide and heterocycle. The influence of reaction conditions (catalyst, base, solvent, and temperature) on conversion of the iodosteroid and the selectivity was investigated. The catalytic system comprising 10 mol-% CuI and 20 mol-% dipivaloylmethane with K₂CO₃ in DMSO at 100 °C delivered the best result. The elaborated protocol has permitted iodosteroids with various substituted indoles, imidazoles, carbazole, indazole, and sec-amides to be coupled, affording the corresponding azolyl-substituted steroids in good to excellent yields. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Computed Properties of C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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 are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Computed Properties of C11H15NO2

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

Pharmacological research on new salicylic and gentisic acid derivatives. III. Influences on pressure and respiration was written by Preziosi, P.;Reduzzi, F.. And the article was included in Archivio Italiano di Scienze Farmacologiche in 1955.Application In Synthesis of N,N-Diethylsalicylamide This article mentions the following:

Only doses above the therapeutic ones caused some transient hypotensive effect (more intense by doses of more than 50 mg./kg.): there was also a connection between the chem. constitution of the drug and the hypotensive effect, as for toxicity. N-diethylsalicylamide caused hypertension after a transient hypotension. As to respiration, diacetylgentisic acid and o-diethylaminoethoxybenzamide caused an increase of the amplitude, and salicoyl hydrazide and salicylamide, at higher doses, its decrease; N-diethylsalicylamide (from 30 mg./kg.) increased the respiratory frequency. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Application In Synthesis of N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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 In Synthesis of N,N-Diethylsalicylamide

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

Tf₂O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides was written by He, Qian;Ye, Jian-Liang;Xu, Fang-Fang;Geng, Hui;Chen, Ting-Ting;Chen, Hang;Huang, Pei-Qiang. And the article was included in Journal of Organic Chemistry in 2021.Reference of 13255-50-0 This article mentions the following:

Ten types of Tf₂O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf₂O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill’s modern version of the Bischler-Napieralski reaction. The value of the Tf₂O/TTBP-based methodol. was further demonstrated by the concise and high-yielding syntheses of several natural products. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Reference of 13255-50-0).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) 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.Reference of 13255-50-0

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

An anomalous Houben-Hoesch reaction and some applications in arylation reactions was written by Sanchez-Viesca, F.;Gomez, Maria R.;Berros, Martha. And the article was included in Organic Preparations and Procedures International in 2004.Quality Control of 2,2-Diethoxyacetamide This article mentions the following:

α,α-Dichloro-2,4,5-trimethoxyacetophenone (1a), prepared via a Houben-Hoesch reaction between 1,2,4-trimethoxybenzene and dichloroacetonitrile, was very unreactive, failing to react with NaOAc, methoxide and ethoxide. Attempted preparation of α,α-diethoxy-2,4,5-trimethoxyacetophenone by Houben-Hoesch reaction of 1,2,4-trimethoxybenzene with diethoxyacetonitrile gave tris(2,4,5-trimethoxyphenyl)methane instead. Reaction of 1,2,4-trimethoxybenzene with diethoxyacetonitrile under Houben-Hoesch conditions gave 2,2-bis(2,4,5-trimethoxyphenyl)acetamide. 2,2-Dichloro-1-methoxy-1-(2,4,5-trimethoxyphenyl)ethane (preparation described) could be arylated by 1,2,4-trimethoxybenzene and 2,4-dimethoxychlorobenzene to give 2,2-dichloro-1,1-bis(2,4,5-trimethoxyphenyl)ethane and 2,2-dichloro-1-(5-chloro-2,4-dimethoxyphenyl)-1-(2,4,5-trimethoxyphenyl)ethane. Reactions of 1,2,4-trimethoxybenzene with RCH₂CN (R = EtO, MeO) under Houben-Hoesch conditions gave 2,4,5-trimethoxyphenacyl chloride (unexpectedly) and α-methoxy-2,4,5-trimethoxyacetophenone, resp. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Quality Control of 2,2-Diethoxyacetamide).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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.Quality Control of 2,2-Diethoxyacetamide

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

New and regioselective synthesis of 4-ylidenetetronic acids by Lewis-acid-catalyzed cyclization of 4-alkoxy-bis-(trimethylsiloxy)-1,3-dienes with oxalyl chloride was written by Langer, Peter;Eckardt, Tobias. And the article was included in Synlett in 2000.Recommanded Product: 106675-70-1 This article mentions the following:

A new approach for the synthesis of 4-ylidenetetronic acids is reported which involves Me₃SiO₃SCF₃-catalyzed regio- and stereoselective cyclization of 4-alkoxy bis(trimethylsiloxy) 1,3-dienes with oxalyl chloride and subsequent chemoselective deprotection of the 3-OH group. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Recommanded Product: 106675-70-1).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) 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. 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: 106675-70-1

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

Design, synthesis, and structure-activity relationship of new isobenzofuranone ligands of protein kinase C was written by Baba, Yoshiyasu;Ogoshi, Yosuke;Hirai, Go;Yanagisawa, Takeshi;Nagamatsu, Kumiko;Mayumi, Satoshi;Hashimoto, Yuichi;Sodeoka, Mikiko. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.COA of Formula: C11H15NO2 This article mentions the following:

Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. PKC ligands having an isobenzofuranone template, based on the proposed interaction of DAG (1,2-diacyl-sn-glycerol) with the PKCδ C1B ligand-binding domain were designed. Several isobenzofuranone derivatives were synthesized and their PKCα binding activities were evaluated. (-)-2,2-Dimethylpropanoic acid [(1R)-4-(dodecyloxy)-1,3-dihydro-1-(hydroxymethyl)-3-oxo-1-isobenzofuranyl]methyl ester (I) was found to be a strong PKCα ligand, and the structure-activity relationship is well explained by our proposed binding model. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2COA of Formula: 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. 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.COA of Formula: C11H15NO2

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

Directing-group-assisted copper-catalyzed oxidative esterification of phenols with aldehydes was written by Zheng, Yong;Song, Wei-Bin;Xuan, Li-Jiang. And the article was included in Organic & Biomolecular Chemistry in 2015.Safety of N,N-Diethylsalicylamide This article mentions the following:

A novel, green and ligand-free approach was developed for the direct synthesis of esters e.g., I, utilizing directing-group-assisted copper-catalyzed oxidative esterification of phenols with aldehydes using TBHP as an oxidant. This methodol. showed the advantages of mild conditions, short routes, excellent functional group tolerance and the use of inexpensive, stable and com. available starting materials. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Safety of N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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 N,N-Diethylsalicylamide

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

Formation of the Tertiary Sulfonamide C(sp³)-N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling was written by Kim, Dong Sun;Lee, Hong Geun. And the article was included in Journal of Organic Chemistry in 2021.Synthetic Route of C9H13NO2S This article mentions the following:

A synthetic strategy for the formation of C(sp³)-N bonds, particularly through a Cu-catalyzed oxidative cross-coupling, is rare. Herein, the authors report a novel synthetic approach for the preparation of tertiary sulfonamides via Cu-catalyzed intra- and intermol. oxidative C(sp³)-N cross-coupling reactions. This method allows the use of the readily available C(sp³)-based pinacol boronate as a substrate and the tolerance of a wide range of functional groups under mild reaction conditions. The success of this strategy relies on the unprecedented additive effects of silanol and NaIO₄. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Synthetic Route of C9H13NO2S).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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.Synthetic Route of C9H13NO2S

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