Tag: 100-200

Tariquidar analogues: synthesis by Cu^I-catalysed N/O-aryl coupling and inhibitory activity against the ABCB1 transporter was written by Egger, Michael;Li, Xuqin;Mueller, Christine;Bernhardt, Guenther;Buschauer, Armin;Koenig, Burkhard. And the article was included in European Journal of Organic Chemistry in 2007.Electric Literature of C11H15NO2 This article mentions the following:

Tariquidar analogs I (R = Br, MeOCH₂CH₂OCH₂CH₂NH, 4-morpholinyl, EtOCH₂CH₂O) are prepared as inhibitors of the ABCB1 transporter using copper-catalyzed coupling reactions of I (R = Br) with 2-(2-methoxyethoxy)ethylamine, morpholine, and 2-ethoxyethanol as the key steps. Ligands and catalysts are tried for the coupling of amines with 5-bromo-2-(tert-butoxycarbonylamino)benzoic acid. Attempted coupling of bis(2-(2-methoxyethoxy)ethyl)amine with I (R = Br) using either palladium or copper catalysts did not give the desired product. The lipophilicities of I (R = Br, MeOCH₂CH₂OCH₂CH₂NH, 4-morpholinyl, EtOCH₂CH₂O) and their inhibition of the ABCB1 transporter in the Kb-V1 human cancer cell line are determined; the lipophilicities of I (R = Br, MeOCH₂CH₂OCH₂CH₂NH, 4-morpholinyl, EtOCH₂CH₂O) correlate with their inhibition of the ABCB1 transporter. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Electric Literature of C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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.Electric Literature of C11H15NO2

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

A facile semi-synthetic approach towards halogen-substituted aminobenzoic acid analogues of platensimycin was written by Qiu, Lin;Tian, Kai;Pan, Jian;Jiang, Lin;Yang, Hu;Zhu, Xiangcheng;Shen, Ben;Duan, Yanwen;Huang, Yong. And the article was included in Tetrahedron in 2017.Formula: C7H7FN2O This article mentions the following:

Platensimycin (PTM), produced by several strains of Streptomyces platensis, is a promising drug lead for infectious diseases and diabetes. The recent pilot-scale production of PTM from S. platensis SB12026 has set the stage for the facile semi-synthesis of a focused library of PTM analogs. In this study, gram-quantity of platensic acid (PTMA) was prepared by the sulfuric acid-catalyzed ethanolysis of PTM, followed by a mild hydrolysis in aqueous lithium hydroxide. Three PTMA esters were also obtained in near quant. yields in a single step, suggesting a facile route to make PTMA aliphatic esters. 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU)-catalyzed coupling of PTMA and 33 aminobenzoates resulted in the synthesis of 28 substituted aminobenzoate analogs of PTM, among which 26 of them were reported for the first time. Several of the PTM analogs showed weak antibacterial activity against methicillin-resistant Staphylococcus aureus. Our study supported the potential utility to integrate natural product biosynthetic and semi-synthetic approaches for structure diversification. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5Formula: C7H7FN2O).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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. 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.Formula: C7H7FN2O

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

Co(II)-Porphyrin Immobilized on Graphene Oxide: An Efficient Catalyst for the Beckmann Rearrangement was written by Ghadamyari, Zohreh;Khojastehnezhad, Amir;Seyedi, Seyed Mohammad;Shiri, Ali. And the article was included in ChemistrySelect in 2019.Safety of 3,4-Dichlorobenzamide This article mentions the following:

In this report, the synthesis of amides from aldoximes (Beckmann rearrangement) has been reported using cobalt(II) porphyrin covalently linked to graphene oxide as a nano heterogeneous catalyst. The prepared catalyst was characterized by applying of FT-IR, TGA, TEM, SEM, EDX, ICP and UV-Vis techniques. All anal. confirm the successful insertion of cobalt into the porphyrin ring and covalently linkage of Co-Porphyrin on the graphene oxide. Moreover, the prepared catalyst was applied in order to investigate its performance in the Beckmann rearrangement. This heterogeneous catalyst exhibited excellent catalytic efficiency with a high yield of products. Also, the suggested catalyst could be recycled for five runs without a dramatic decrease in its catalytic activity or metal leaching. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Safety of 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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. 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 3,4-Dichlorobenzamide

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

Design, synthesis and biological activity of ethyl 2-(N-substituted-arylsulfonamido)-2-oxo-acetate was written by Wang, Bao-lei;Wu, Jing;He, Feng-qi;Li, Yong-hong;Li, Zheng-ming. And the article was included in Chemical Research in Chinese Universities in 2008.Electric Literature of C9H13NO2S This article mentions the following:

Thirteen new Et 2-(N-substituted-arylsulfonamido)-2-oxo-acetates, based on the structure of ketol-acid reductoisomerase (KARI) inhibitor IpOHA, were designed and synthesized. Their structures were established on the basis of ¹H NMR, IR, MS, and elemental analyses. The bioassay result reveals that the structural changes from hydroxyl group on the N atom of IpOHA to arylsulfonyl groups does not enhance the inhibitory activity of the compounds to KARI in vitro. Compounds 2-(N-isopropyl/phenyl/p-chlorophenyl-(2-nitrophenyl/p-methylphenyl/phenyl)sulfonamido)-2-oxo-acetates are more effective than IpOHA against the monocotyledonous barnygrass at 100 μg/mL in herbicidal tests. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Electric Literature of C9H13NO2S).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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 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.Electric Literature of C9H13NO2S

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

Design of inhibitors from the three-dimensional structure of alcohol dehydrogenase. Chemical synthesis and enzymic properties was written by Freudenreich, Charles;Samama, Jean Pierre;Biellmann, Jean Francois. And the article was included in Journal of the American Chemical Society in 1984.Category: amides-buliding-blocks This article mentions the following:

Inhibitors of liver alc. dehydrogenase were designed from the 3-dimensional structure of the enzyme. The ligand to the catalytic Zn(II) is an amide group or, better, a formamide group. With the latter function, a H-bond between the NH groups and the hydroxyl group of serine-48 may be formed. The hydrophobic substrate binding site brings structural restraints. α-ω Bifunctional mols. show good inhibitory properties possibly due to the interactions with polar residues at the entrance of the substrate. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Category: amides-buliding-blocks).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) 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

Mechanochemical Divergent Syntheses of Oxindoles and α-Arylacylamides via Controllable Construction of C-C and C-N Bonds by Copper and Piezoelectric Materials was written by Lv, Honggui;Xu, Xinyue;Li, Jing;Huang, Xiaobo;Fang, Guoyong;Zheng, Lifei. And the article was included in Angewandte Chemie, International Edition in 2022.HPLC of Formula: 5339-69-5 This article mentions the following:

The divergent syntheses of α-arylacylamides Ar(C)R¹R²C(O)NHAr/Alkyl (Ar = Ph, 2,3-dihydro-1-benzofuran-5-yl, naphthalen-1-yl, thiophen-2-yl, etc.; R¹ = Me, H; R² = Me, F; R¹R² = cyclobutyl; Alkyl = Me, 2-methylpropyl, butyl) and oxindoles I (R³ = Me; R⁴ = Me; R³R⁴ = cyclobutyl; Alkyl = Me, 2-methylpropyl) via mechanoredox chem. by using easily accessible α-bromo N-sulfonyl amides ArS(O)₂(N)alkylC(O)CR²R³X as starting materials were present. The system consists of a catalytic amount of Cu^II precatalyst and piezoelec. materials. The highly polarized BaTiO₃ or PbTiO₃ under mech. agitation can act as an electron donor to realize the recycling of Cu^II and Cu^I. Control experiments and d. functional theory calculations have been performed to support the proposed mechanistic rationale for the cascade reactions. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5HPLC of Formula: 5339-69-5).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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 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.HPLC of Formula: 5339-69-5

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

Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets was written by Mayhoub, Abdelrahman S.;Marler, Laura;Kondratyuk, Tamara P.;Park, Eun-Jung;Pezzuto, John M.;Cushman, Mark. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Reference of 2670-38-4 This article mentions the following:

Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biol. targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1). In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Reference of 2670-38-4).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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.Reference of 2670-38-4

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

Convenient cyclization of o-difunctional heterocycles with N,N-dimethylformamide dimethyl acetal was written by Stanovnik, B.;Tisler, M.. And the article was included in Synthesis in 1974.Reference of 50608-99-6 This article mentions the following:

0-Phenylenediamine cyclized readily with Me2NCH(OMe)2 when heated at 120-30° for 2 hr in DMF to give benzimidazole I (X = NH, X1 = CH). Analogously I (X = S, X1 = CH; X = S, X1 = N; X = NH X1 = N), II, and III (X = N, X1 = CH; X = CH, X1 = ) were prepared In the experiment, the researchers used many compounds, for example, 3-Aminopicolinamide (cas: 50608-99-6Reference of 50608-99-6).

3-Aminopicolinamide (cas: 50608-99-6) 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. 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.Reference of 50608-99-6

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

A new and efficient synthetic route for the anxiolytic agent CL285032 was written by Ghidu, Victor P.;Ilies, Marc A.;Cullen, Tom;Pollet, Robert;Abou-Gharbia, Magid. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Synthetic Route of C11H13NO2 This article mentions the following:

CL285032, i.e. 6-[3-(acetylmethylamino)phenyl]-3-methyl[1,2,4]triazolo[4,3-b]pyridazine, is an anxiolytic compound currently under investigation as a possible treatment for canine noise phobia associated anxiety. A robust scale-up and manufacturing process is essential for the development and marketability of the drug. The current synthetic route, although reliable, requires 7 steps and has a low overall yield (18%), leaving opportunity for improvement. The authors present an efficient alternative approach toward the synthesis of CL285032 from 3-AcMeNC₆H₄Ac over 3 steps with 65% overall yield. In the experiment, the researchers used many compounds, for example, N-(3-Acetylphenyl)-N-methylacetamide (cas: 325715-13-7Synthetic Route of C11H13NO2).

N-(3-Acetylphenyl)-N-methylacetamide (cas: 325715-13-7) 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. 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.Synthetic Route of C11H13NO2

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

Directed ortho Metalation (DoM)-Linked Corriu-Kumada, Negishi, and Suzuki-Miyaura Cross-Coupling Protocols: A Comparative Study was written by Quesnelle, Claude A.;Snieckus, Victor. And the article was included in Synthesis in 2018.Application In Synthesis of N,N-Diethylsalicylamide This article mentions the following:

A systematic study of the widely used, titled transition-metal-catalyzed cross-coupling reactions with attention to context with the directed orthometalation (DoM) was reported. In general, the Suzuki-Miyaura and Negishi protocols showed greater scope and better yields than the Corriu-Kumada variant, although the latter qual. proceeded at fastest rate but had low functional group tolerance. The Negishi process was shown to be useful for substrates with nucleophile and base-sensitive functionality and it was comparable to the Suzuki-Miyaura reaction in efficiency. The link of these cross-coupling reactions to the DoM strategy lends itself to the regioselective construction of diversely substituted aromatics and heteroaromatics 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. 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.Application In Synthesis of N,N-Diethylsalicylamide

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