Tag: 100-200

Design, synthesis, and biological evaluation of quinazolin-4(3H)-one derivatives co-targeting poly(ADP-ribose) polymerase-1 and bromodomain containing protein 4 for breast cancer therapy was written by Chang, Xiaosa;Sun, Dejuan;Shi, Danfeng;Wang, Guan;Chen, Yanmei;Zhang, Kai;Tan, Huidan;Liu, Jie;Liu, Bo;Ouyang, Liang. And the article was included in Acta Pharmaceutica Sinica B in 2021.Computed Properties of C9H12N2O3 This article mentions the following:

This study was aimed to design the first dual-target small-mol. inhibitor co-targeting poly (ADP-ribose) polymerase-1 (PARP1) and bromodomain containing protein 4 (BRD4), which had important cross relation in the global network of breast cancer, reflecting the synthetic lethal effect. A series of new BRD4 and PARP1 dual-target inhibitors I [R¹ = H, 4,6-(OMe)₂; R² = C(O)NH₂, C(O)NHMe, etc.], II [R³ = H, 5-OMe, 4,6-(OMe)₂; n₁ = 0,1], III [R⁴ = H, 5-OMe, 4,6-(OMe)₂; R⁵ = 4-(cyclopropanecarbonyl)piperazine-1-carbonyl, 3-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolyl], IV [R⁶ = Cl, 3-F, 3-Cl, etc.; R⁷ = 2-benzamidyl, 1H-benzo[d][1,2,3]triazol-1-yl, 1H-indazol-6-yl, etc.; n₂ = 1,2,3,4,5] were discovered and synthesized by fragment-based combinatorial screening and activity assays that together led to the chem. optimization. Among these compounds, IV [R⁶ = H; R⁷ = 2-benzamidyl; n₂ = 2] was selected and exhibited micromole enzymic potencies against BRD4 and PARP1, resp. Compound IV [R⁶ = H; R⁷ = 2-benzamidyl; n₂ = 2] was further showed to efficiently modulate the expression of BRD4 and PARP1. Subsequently, compound IV [R⁶ = H; R⁷ = 2-benzamidyl; n₂ = 2] was found to induce breast cancer cell apoptosis and stimulate cell cycle arrest at G1 phase. Following pharmacokinetic studies, compound IV [R⁶ = H; R⁷ = 2-benzamidyl; n₂ = 2] showed its antitumor activity in breast cancer susceptibility gene 1/2 (BRCA1/2) wild-type MDA-MB-468 and MCF-7 xenograft models without apparent toxicity and loss of body weight These results together demonstrated that a highly potent dual-targeted inhibitor was successfully synthesized and indicated that co-targeting of BRD4 and PARP1 based on the concept of synthetic lethality would be a promising therapeutic strategy for breast cancer. In the experiment, the researchers used many compounds, for example, 2-Amino-4,6-dimethoxybenzamide (cas: 63920-73-0Computed Properties of C9H12N2O3).

2-Amino-4,6-dimethoxybenzamide (cas: 63920-73-0) 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.Computed Properties of C9H12N2O3

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

Amberlyst A26 OH as a recyclable catalyst for hydration of nitriles and water-based synthesis of 4(1H)-quinazolinones from 2-aminobenzonitrile and carbonyl compounds was written by Tamaddon, Fatemeh;Pouramini, Farzaneh. And the article was included in Synlett in 2014.Quality Control of 2-(2-Chlorophenyl)acetamide This article mentions the following:

Selective hydration of nitriles to primary amides as well as the base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones, e.g., I, via reaction of 2-aminobenzonitrile with carbonyl compounds using macroporous Amberlyst A26 OH in H₂O-EtOH is described. The latter reaction proceeds via tandem hydration of 2-aminobenzonitrile, condensation of the in situ generated 2-aminobenzamide with carbonyl compounds, and cyclization of the imine intermediate to give the quinazolinone derivatives In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Quality Control of 2-(2-Chlorophenyl)acetamide).

2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) 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. 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.Quality Control of 2-(2-Chlorophenyl)acetamide

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

Synthesis and biological evaluation of 1,2,4-oxadiazole core derivatives as potential neuroprotectants against acute ischemic stroke was written by Shi, Jinguo;Wang, Yang;Chen, Jianwen;Lao, Yaoqiang;Huang, Ping;Liao, Liping;Jiang, Caibao;Li, Xinhua;Wen, Jin;Zhou, Shujia;Zhang, Jingxia. And the article was included in Neurochemistry International in 2021.Recommanded Product: 49667-22-3 This article mentions the following:

Here, we report the synthesis and neuroprotective capacity of 27 compounds with a bisphenol hydroxyl-substituted 1,2,4-triazole core or 1,2,4-oxadiazole core for stroke therapy. In vitro studies of the neuroprotective effects of compounds 1-27 on sodium nitroprusside (SNP)-induced apoptosis in PC12 cells indicate that compound 24 is the most effective compound conferring potent protection against oxidative injury. Compound 24 inhibits reactive oxygen species (ROS) accumulation and restores the mitochondrial membrane potential (MMP). Moreover, further anal. of the mechanism showed that compound 24 activates the antioxidant defense system by promoting the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2) and increasing the expression of haem oxygenase 1 (HO-1). An in vivo study was performed in a rat model of transient focal cerebral ischemia generated by the intraluminal occlusion of the middle cerebral artery (MCAO). Compound 24 significantly reduced brain infarction and improved neurol. function. Overall, compound 24 potentially represents a promising compound for the treatment of stroke. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-4-methylbenzamide (cas: 49667-22-3Recommanded Product: 49667-22-3).

2-Hydroxy-4-methylbenzamide (cas: 49667-22-3) 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. 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.Recommanded Product: 49667-22-3

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

Synthesis of 3,4-difluorobenzonitrile and monofluorobenzonitriles by means of halogen-exchange fluorination was written by Suzuki, Hiroshi;Kimura, Yoshikazu. And the article was included in Journal of Fluorine Chemistry in 1991.Application of 2670-38-4 This article mentions the following:

3,4-Difluorobenzonitrile has been prepared by a halogen-exchange reaction between 3,4-dichlorobenzonitrile and spray-dried potassium fluoride in the presence of tetraphenylphosphonium bromide in refluxing 1,3-dimethylimidazolidine-2-one (DMI). In the fluorination reaction, 4-chloro-3-fluorobenzonitrile seems to be a key intermediate. 2-, 3-, And 4-fluorobenzonitriles have also been produced from the corresponding chlorobenzonitriles by halogen-exchange at 290° in DMI in a pressure reactor. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Application 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. 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.Application of 2670-38-4

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

Synthesis of the NK1 Receptor Antagonist GW597599. Part 1: Development of a Scalable Route to a Key Chirally Pure Arylpiperazine was written by Guercio, Giuseppe;Bacchi, Sergio;Goodyear, Michael;Carangio, Antonella;Tinazzi, Francesco;Curti, Stefano. And the article was included in Organic Process Research & Development in 2008.Electric Literature of C6H12N2O4 This article mentions the following:

GW597599 is a NK-1 antagonist under study for treatment of CNS disorders and emesis. The initial synthetic route devised from the medicinal chem. route, used several hazardous reagents, gave low yields, and produced high levels of wastes. By targeted process of research and development, application of novel techniques, and extensive route scouting, a synthetic route for GW597599 was developed. The optimization of the first stage in the chem. synthesis of GW597599 is described: the development of a pilot-plant process for the synthesis of arylpiperazine derivative as optically pure compound The method eliminates the initial need for cryogenic conditions and copper catalysis in Grignard chem. and allows replacing the classical resolution step with a more efficient dynamic kinetic resolution, substantially enhancing the overall yield and throughput. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Electric Literature of C6H12N2O4).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) 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.Electric Literature of C6H12N2O4

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

Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups was written by O’Mahony, Gavin;Pitts, Andrew K.. And the article was included in Organic Letters in 2010.Product Details of 19311-91-2 This article mentions the following:

In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%). In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Product Details of 19311-91-2).

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

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

Pharmacological research on new salicylic and gentisic acid derivatives. II. Antipyretic, antialgic, antihyaluronidase, antipermeability, and antiexudative activity was written by Preziosi, P.. And the article was included in Archivio Italiano di Scienze Farmacologiche in 1955.Synthetic Route of C11H15NO2 This article mentions the following:

The various properties for all substances of part I are tabulated with the aim of evaluating their antirheumatic activity: it is concluded that N-diethylsalicylamide, o-ethoxybenzamide, and gentisamide are more active than salicylamide. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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 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.Synthetic Route of C11H15NO2

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

Structure-activity relationship of pyrrole based S-nitrosoglutathione reductase inhibitors: Carboxamide modification was written by Sun, Xicheng;Qiu, Jian;Strong, Sarah A.;Green, Louis S.;Wasley, Jan W. F.;Blonder, Joan P.;Colagiovanni, Dorothy B.;Stout, Adam M.;Mutka, Sarah C.;Richards, Jane P.;Rosenthal, Gary J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Quality Control of 4-Amino-3-methylbenzenesulfonamide This article mentions the following:

The enzyme S-nitrosoglutathione reductase (GSNOR) is a member of the alc. dehydrogenase family (ADH) that regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). GSNO and SNOs are implicated in the pathogenesis of many diseases including those in respiratory, gastrointestinal, and cardiovascular systems. The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious GSNOR inhibitor which is currently in clin. development for acute asthma. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogs of N6022 focusing on carboxamide modifications on the pendant N-Ph moiety. We have identified potent and novel GSNOR inhibitors that demonstrate efficacy in an ovalbumin (OVA) induced asthma model in mice. In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Quality Control of 4-Amino-3-methylbenzenesulfonamide).

4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4) 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. 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.Quality Control of 4-Amino-3-methylbenzenesulfonamide

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

Discovery of BMS-986202: A Clinical Tyk2 Inhibitor that Binds to Tyk2 JH2 was written by Liu, Chunjian;Lin, James;Langevine, Charles;Smith, Daniel;Li, Jianqing;Tokarski, John S.;Khan, Javed;Ruzanov, Max;Strnad, Joann;Zupa-Fernandez, Adriana;Cheng, Lihong;Gillooly, Kathleen M.;Shuster, David;Zhang, Yifan;Thankappan, Anil;McIntyre, Kim W.;Chaudhry, Charu;Elzinga, Paul A.;Chiney, Manoj;Chimalakonda, Anjaneya;Lombardo, Louis J.;Macor, John E.;Carter, Percy H.;Burke, James R.;Weinstein, David S.. And the article was included in Journal of Medicinal Chemistry in 2021.Electric Literature of C8H9ClN2O This article mentions the following:

A search for structurally diversified Tyk2 JH2 ligands from 6 (BMS-986165), a pyridazine carboxamide-derived Tyk2 JH2 ligand as a clin. Tyk2 inhibitor currently in late development for the treatment of psoriasis, began with a survey of six-membered heteroaryl groups in place of the N-Me triazolyl moiety in 6. The x-ray co-crystal structure of an early lead (12) revealed a potential new binding pocket. Exploration of the new pocket resulted in two front-runners for a clin. candidate. The potential hydrogen bonding interaction with Thr599 in the pocket was achieved with a tertiary amide moiety, confirmed by the x-ray co-crystal structure of 29. When the diversity search was extended to nicotinamides, a single fluorine atom addition was found to significantly enhance the permeability, which directly led to the discovery of 7 (BMS-986202) as a clin. Tyk2 inhibitor that binds to Tyk2 JH2. The preclin. studies of 7, including efficacy studies in mouse models of IL-23-driven acanthosis, anti-CD40-induced colitis, and spontaneous lupus, will also be presented. In the experiment, the researchers used many compounds, for example, 6-Chloro-N,N-dimethylnicotinamide (cas: 54864-83-4Electric Literature of C8H9ClN2O).

6-Chloro-N,N-dimethylnicotinamide (cas: 54864-83-4) 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 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 C8H9ClN2O

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

Infrared spectra of N-substituted sulfonamides was written by Goldstein, Michael;Russell, Maurice Alan;Willis, H. A.. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 1969.Name: N-Isopropylbenzenesulfonamide This article mentions the following:

The ir spectra of 25 sulfonamides of the types MeSO2NHR (R = Me, iso-Pr, tert-Bu) MeSO2NR2 (R = Me,Et,iso-Pr), ArSO2NHR (Ar = Ph, p-tolyl; R = Me, Et, Pr, iso-Pr, Bu, iso-Bu, sec-Bu, tert-Bu), and PhSO2NR2 (R = Me, Et, iso-Pr) have been studied. Assignments are discussed for stretching and deformation vibrations of the NH and SO2 groups and for SN, CS and CN stretching modes. Some consideration is also given to vibrations of the hydrocarbon residues. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Name: N-Isopropylbenzenesulfonamide).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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.Name: N-Isopropylbenzenesulfonamide

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