Month: January 2023

Cleavage of the C-C triple bond of ketoalkynes: synthesis of 4(3H)-quinazolinones was written by Yang, Xifa;Cheng, Guolin;Shen, Jinhai;Kuai, Changsheng;Cui, Xiuling. And the article was included in Organic Chemistry Frontiers in 2015.Category: amides-buliding-blocks This article mentions the following:

A novel protocol for the synthesis of 4(3H)-quinazolinones I (R¹ = H, 6-Me, 7-Me, 5-F, etc.; R² = H, n-hexyl, Ph, 2-MeC₆H₄, 2-thienyl, etc.; R³ = H, Me, Ph) from o-amino benzamides II and alkynyl ketones R²CCC(O)Ph under oxidant-, metal-, and ligand-free conditions has been developed. The process includes selective cleavage of the C-C triple bond of alkynyl ketones and formation of two C-N bonds. 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. 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 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.Category: amides-buliding-blocks

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

Sulfonylurea receptor 1-expressing cancer cells induce cancer-associated fibroblasts to promote non-small cell lung cancer progression was written by Chen, Hongling;Zhao, Li;Meng, Yuting;Qian, Xixi;Fan, Ya;Zhang, Quanli;Wang, Chao;Lin, Fan;Chen, Baoan;Xu, Lin;Huang, Wenbin;Chen, Jing;Wang, Xuerong. And the article was included in Cancer Letters (New York, NY, United States) in 2022.Reference of 10238-21-8 This article mentions the following:

Cancer-associated fibroblasts (CAFs) play a pivotal role in cancer progression; however, how CAFs are induced remains elusive. Sulfonylurea receptor 1 (SUR1) is a tumor-enhancer in non-small cell lung carcinoma (NSCLC). Here, we probed the influence of SUR1-expressing cancer cells on CAFs. Results showed that high SUR1 expression pos. correlated with α-SMA pos. staining of CAFs in tumor tissues and poor prognosis of NSCLC patients. SUR1 contributed to normal fibroblast (NF) transformation into CAFs and facilitated the growth and metastasis of NSCLC in vivo. Conditioned medium (CM) and exosomes from SUR1-expressing cancer cells induced CAFs and promoted fibroblast migration. In cancer cells, SUR1 promoted p70S6K-induced KH-type splicing regulatory protein (KHSRP) phosphorylation at S395 to inhibit the binding of KHSRP with let-7a precursor (pre-let-7a) and decreasing mature let-7a-5p expression in cancer cells and exosomes. Let-7a-5p delivered by exosomes blocked NF transformation into CAFs by targeting TGFBR1 to inactivate the TGF-β signaling pathway. Glibenclamide, which targets SUR1, restrained CAFs and suppressed tumor growth in patient-derived xenograft models. Furthermore, we found that let-7a-5p was decreased in the tissues and plasma exosomes of NSCLC patients. In summary, SUR1-expressing cancer cells induce NF transformation into CAFs in the tumor microenvironment and promote NSCLC progression by transferring less exosomal let-7a-5p. Glibenclamide is a promising anti-cancer drug, and plasma exosomal let-7a-5p level is a potential diagnostic biomarker for NSCLC patients. These findings provide new therapeutic strategies by targeting SUR1 in NSCLC. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Reference of 10238-21-8).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) 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.Reference of 10238-21-8

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

Immunomodulatory and immunosuppressive therapies in cardiovascular disease and type 2 diabetes mellitus: A bedside-to-bench approach was written by Mikkelsen, Rasmus R.;Hundahl, Malthe P.;Torp, Christopher K.;Rodriguez-Carrio, Javier;Kjolby, Mads;Bruun, Jens M.;Kragstrup, Tue W.. And the article was included in European Journal of Pharmacology in 2022.Recommanded Product: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide This article mentions the following:

To assess which immunosuppressive drugs have been investigated and proven efficacious in patients with cardiovascular disease (CVD) or type 2 diabetes (T2D) without preexisting immune mediated disorders to validate in vitro and animal model findings on low grade inflammation (bedside-to-bench). Clin. trials on immunosuppressive drugs in CVD or T2D were found in PubMed. Studies on patients with preexisting immune mediated inflammatory disease were excluded. A total of 19 clin. trials testing canakinumab, anakinra, methotrexate, colchicine, hydroxychloroquine, etanercept and sulfasalazine were found. Canakinumab and colchicine significantly reduced the risk of CVD, whereas methotrexate did not. Sulfasalazine showed no effect on vascular function. Anakinra and hydroxychloroquine had a pos. effect on glycemic control and β-cell function in T2D. Etanercept had no effect in patients with T2D. The observed results indicate that immunosuppressive drugs specifically targeting IL-1β hold promise for dampening CVD and T2D. These findings validate in vitro and animal models showing involvement of the IL-1-axis in the pathogenesis of CVD and T2D. The use of immunosuppressive drugs targeting the chronic inflammation in these diseases could be a possible future treatment strategy as an add-on to the existing pharmacol. treatment of CVD and T2D. However, potential treatment effects, adverse events and cost-effectiveness should be carefully considered with importance for drug development. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Recommanded Product: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) 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. 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.Recommanded Product: 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

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

Effect of various cryoprotectants on freeze-drying of liposomes containing Na methotrexate was written by Toliat, T.;Arab, N.;Rafiee-Tehrani, M.. And the article was included in Proceedings of the International Symposium on Controlled Release of Bioactive Materials in 1998.SDS of cas: 7413-34-5 This article mentions the following:

The retention of sodium methotrexate from liposomes after freeze-drying enhanced with the presence of sugars and polymers. Trehalose and Me cellulose had the most effective preservation against leakage form liposomes after lyophilization. In the experiment, the researchers used many compounds, for example, Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5SDS of cas: 7413-34-5).

Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5) 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 freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.SDS of cas: 7413-34-5

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

Synthesis and geometric configuration of 2-(hydroxyiminomethyl)thiazole-4-carboxylic acid in antibiotic althiomycin was written by Shiba, Tetsuo;Inami, Kaoru;Sawada, Kozo;Hirotsu, Yoshihiro. And the article was included in Heterocycles in 1979.Product Details of 61189-99-9 This article mentions the following:

Isomeric oximes I (R = Et) were prepared from (EtO)₂CHCO₂Et in 6 steps. The isomers were separated and their configuration determined by nuclear Overhauser enhancement. These assignments were used to established that I (R = H) in althiomycin have the syn configuration and it isomerized on purification on acid ion exchange resin. Althiomycin has the syn configuration II. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Product Details of 61189-99-9).

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

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

Photochemical properties and degradation by-products of triasulfuron and thifensulfuron-methyl was written by Scrano, Laura;Bufo, Sabino A.;D’Auria, Maurizio;Chovelon, Jean-Marc. And the article was included in International Journal of Environmental Analytical Chemistry in 2006.Recommanded Product: 2-(2-Chloroethoxy)benzenesulfonamide This article mentions the following:

The effect of light on two sulfonylurea herbicides, triasulfuron and thifensulfuron Me, was studied under both UV and solar simulator irradiation (Suntest). Energies of first singlet and triplet state transitions were calculated from fluorescence and phosphorescence spectra. Experiments were performed in the presence of either a singlet or a triplet quencher showing that photodegradation of both herbicides begins from a triplet state, T₁. The photolysis process of both herbicides occurred through first-order kinetics. The investigation stressed the relevance of the light exposition on the degradation rate of both herbicides. Half-lives of photolysis reactions (Suntest) in the organic solvent used in the experiments (22 and 54 h for triasulfuron and thifensulfuron Me, resp.) are comparable with the hydrolysis rate in aqueous environment. With UV irradiation, the degradation time of both herbicides can be greatly reduced to several minutes, thus suggesting that this technique can be adopted as an efficient method of detoxification. The main photoproducts, identified by LC-ESI-MS, were: (4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea and 4-methoxy-6-methyl-1,3,5-triazin-2-amine, common to triasulfuron and thifensulfuron-methyl; 2-(2-chloroethoxy)benzenesulfonamide and (2-chloroethoxy)benzene, arising from triasulfuron degradation; 4-sulfamoyl-thiophene-3-carboxylic acid Me ester and thiophene-3-carboxylic acid Me ester, occurring from thifensulfuron-Me transformation. The presence of minor byproducts was also ascertained. In the experiment, the researchers used many compounds, for example, 2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6Recommanded Product: 2-(2-Chloroethoxy)benzenesulfonamide).

2-(2-Chloroethoxy)benzenesulfonamide (cas: 82097-01-6) 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. 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.Recommanded Product: 2-(2-Chloroethoxy)benzenesulfonamide

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

Microchannel-embedded implantable device with fibrosis suppression for prolonged controlled drug delivery was written by Ji, Han Bi;Hong, Jae Young;Kim, Cho Rim;Min, Chang Hee;Han, Jae Hoon;Kim, Min Ji;Kim, Se-Na;Lee, Cheol;Choy, Young Bin. And the article was included in Drug Delivery in 2022.HPLC of Formula: 53902-12-8 This article mentions the following:

For the prolonged, controlled delivery of systemic drugs, we propose an implantable drug-delivery chip (DDC) embedded with pairs of a microchannel and drug-reservoir serving as a drug diffusion barrier and depot, resp. We pursued a DDC for dual drugs: a main-purpose drug, diclofenac (DF), for systemic exposure, and an antifibrotic drug, tranilast (TR), for local delivery. Thus, the problematic fibrotic tissue formation around the implanted device could be diminished, thereby less hindrance in systemic exposure of DF released from the DDC. First, we sep. prepared DDCs for DF or TR delivery, and sought to find a proper microchannel length for a rapid onset and sustained pattern of drug release, as well as the required drug dose. Then, two distinct DDCs for DF and TR delivery, resp., were assembled to produce a Dual_DDC for the concurrent delivery of DF and TR. When the Dual_DDC was implanted in living rats, the DF concentration in blood plasma did not drop significantly in the later periods after implantation relative to that in the early periods before fibrotic tissue formation. When the Dual_DDC was implanted without TR, there was a significant decrease in the blood plasma DF concentration as the time elapsed after implantation. Biopsied tissues around the Dual_DDC exhibited a significant decrease in the fibrotic capsule thickness and collagen d. relative to the Dual_DDC without TR, owing to the effect of the local, sustained release of the TR. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8HPLC of Formula: 53902-12-8).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) 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. 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.HPLC of Formula: 53902-12-8

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

Evaluation of the toxicity and teratogenicity of drugs was written by Gastol-Lewinska, Lidia. And the article was included in Polish Journal of Pharmacology and Pharmacy in 1973.Formula: C20H20N8Na2O5 This article mentions the following:

Amethopterin Na (I Na salt) [7413-34-5] (0.001 mg/egg) was highly embryotoxic; allobarbital [52-43-7] (0.5 mg/egg), phenobarbital Na [57-30-7] (0.5 mg/egg), tolbutamide [64-77-7] (1.0 mg/egg), and insulin [9004-10-8] (1 IU) were slightly embryotoxic; and barbital Na [144-02-5] was not embryotoxic for White Leghorn chicken embryos between 50-56 hr of incubation. Allobarbital, phenobarbital and insulin produced malformations, but amethopterin, barbital, and tolbutamide were not teratogenic for chickens. In the experiment, the researchers used many compounds, for example, Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5Formula: C20H20N8Na2O5).

Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5) 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. 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: C20H20N8Na2O5

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

The action of mixed organomagnesium compounds on several aromatic amides with hydroxyl or alkoxyl groups was written by Couturier, Paul. And the article was included in Compt. rend. in 1937.Formula: C11H15NO2 This article mentions the following:

Under conditions in which EtMgBr reacts with o-HOC₆H₄CONEt₂ to give 85% ketone and with the p-isomer to give 5%, it reacts with the corresponding 2,4-di-OH compound to give 10% 2,4-dihydroxypropiophenone. The diethylamides of o- and p-MeOC₆H₄CO₂H (I), 3,4-dihydroxy- and 3,4,5-trihydroxybenzoic acid (II) give with EtMgBr 60-80% of mono-, di- or trimethoxypropiophenones. The diethylamide of anisic acid gives the corresponding ketone and also Et₂NCPh₂C₆H₄OMe which is decomposed by acids to Et₂NH and HOCPh₂C₆H₄OMe. Simple amides of I and II with EtMgBr give 70% of the same ketones, mixed with the corresponding imides, which m. 45° and 48°, resp. 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. 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.Formula: C11H15NO2

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

Green Microwave-Assisted Synthesis of Cyclic/Acyclic Ureas from Propylene Carbonate was written by Qaroush, Abdussalam K.;Alsayyed, Ahed W.;Eftaiha, Ala’a F.;Al-Qaisi, Feda’a M.;Salameh, Bader A.. And the article was included in ChemistrySelect in 2022.Application In Synthesis of 1,3-Dicyclohexylurea This article mentions the following:

Herein, an organocatalyzed synthetic pathway for the preparation of acyclic ureas RHNC(O)NHR (R = Bu, sec-Bu, Ph, cyclohexyl, cyclohexylmethyl, benzyl)/cyclic ureas I (n = 1, 2) from their parent primary aliphatic or aromatic monoamines NH₂(CH₂)_nCH₂NH₂/diamines RNH₂ with propylene carbonate as a carbonylating agent obtaining reasonable to very good yields with high selectivity has been described. This method is considered green as nine out of twelve green chem. principles (GCPs) are fulfilled. Most importantly, the absence of solvent and, energy-efficient pathway, in addition to the ease of synthesis and separation, under fast reaction times down to a few minutes together with the straightforward workup with min. use of organic solvents are described. This method was successful in preparing 1,3-diphenylurea from aniline giving 8% yield in 10 min, which was not previously reported using aromatic amines with carbonate esters. The method is applicable for primary rather than secondary amines, which implies high chemoselectivity of the former for the synthesis of urea compounds In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application In Synthesis of 1,3-Dicyclohexylurea).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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.Application In Synthesis of 1,3-Dicyclohexylurea

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