Month: December 2022

N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites was written by Chandrabalan, Arundhasa;McPhillie, Martin J.;Morice, Alyn H.;Boa, Andrew N.;Sadofsky, Laura R.. And the article was included in European Journal of Medicinal Chemistry in 2019.Name: 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitizing effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Name: 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid).

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

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

Development of an in vitro cholestatic drug-induced liver injury evaluation system using HepG2-hNTCP-C4 cells in sandwich configuration was written by Sakai, Yoko;Okumura, Hiroki;Iwao, Takahiro;Watashi, Koichi;Ito, Kousei;Matsunaga, Tamihide. And the article was included in Toxicology In Vitro in 2019.Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

Toxicol. approaches in screening drugs that cause drug-induced liver injury (DILI) are urgently needed to reduce the risk of developing DILI and avoid immense costs resulting from late-stage drug withdrawal from clin. trials. Cholestatic DILI is characterized by bile acid (BA) accumulation in hepatocytes, typically caused by drug-induced inhibition of important bile transporters, such as bile salt export pump (BSEP) and multidrug resistance-associated protein 2/3/4 (MRP2/3/4). Therefore, NTCP expression is essential for construction of an in vitro hepatocellular toxicity evaluation system. Here, we investigated whether sandwich-cultured HepG2-hNTCP-C4 (SCHepG2-hNTCP-C4) cells were applicable for evaluation of cholestatic DILI. In SCHepG2-hNTCP-C4 cells, NTCP and MRP2/4 expression levels were comparable to those in human primary hepatocytes; however, BSEP expression was low. In addition, the substrates tauro-nor-THCA-24 DBD and CDF confirmed the functionality of NTCP and MRP2, resp. When 22 known hepatotoxins were exposed to BAs to evaluate cholestatic DILI, cytotoxicity in SCHepG2-hNTCP-C4 cells was more frequent than that in SCHepG2 cells. Thus, SCHepG2-hNTCP-C4 cells may be useful preclin. screening tools to predict the risk of cholestatic DILI induced by drug candidates. However, further studies are needed to determine why the cholestatic cytotoxicity of some compounds would be still insufficient in SCHepG2-hNTCP-C4 cells. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) 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. 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.Application In Synthesis of 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

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

Bromination of 4-arenesulfonamidophenols and -1-naphthols and N-(arylsulfonyl)-1,4-benzo(naphtho)quinone 4-imines was written by Avdeenko, A. P.;Velichko, N. V.. And the article was included in Zhurnal Organicheskoi Khimii in 1992.Product Details of 1146-43-6 This article mentions the following:

2,3,6-Tribromo-N-arylsulfonyl-1,4-benzoquinon-4-imines are formed by bromination of 4-arenesulfonamidophenols and N-arylsulfonyl-1,4-benzoquinon-4-imines, but in the case of 4-arenesulfonamido-1-naphthols and N-arylsulfonyl-1,4-naphthoquinon-4-imines only 2-bromo-N-arylsulfonyl-1,4-naphthquinon-4-imines are formed. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Product Details of 1146-43-6).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) 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. 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.Product Details of 1146-43-6

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

Cytotoxic effects of dental calculus particles and freeze-dried Aggregatibacter actinomycetemcomitans and Fusobacterium nucleatum on HSC-2 oral epithelial cells and THP-1 macrophages was written by Ziauddin, S. M.;Alam, Mohammad Ibtehaz;Mae, Megumi;Oohira, Masayuki;Higuchi, Kanako;Yamashita, Yasunori;Ozaki, Yukio;Yoshimura, Atsutoshi. And the article was included in Journal of Periodontology in 2022.Synthetic Route of C23H28ClN3O5S This article mentions the following:

Background : Periodontitis is an inflammatory disease initiated by dental deposits. Microorganisms in the dental biofilm induce cell death in epithelial cells, contributing to the breakdown of epithelial barrier function. Recently, dental calculus has also been implicated in pyroptotic cell death in oral epithelium. We analyzed the cytotoxic effects of dental calculus and freeze-dried periodontopathic bacteria on oral epithelial cells and macrophages. Methods : HSC-2 (human oral squamous carcinoma cells) and phorbol 12-myristate 13-acetate-differentiated THP-1 macrophages were exposed to dental calculus or one of two species of freeze-dried bacterium, Aggregatibacter actinomycetemcomitans and Fusobacterium nucleatum. Following incubation for 24 h, we measured cytotoxicity via lactate dehydrogenase release. Cells were then incubated with glyburide, an NLRP3 inflammasome inhibitor, to assess the potential role of pyroptosis. We also conducted a permeability assay to analyze the effects on epithelial barrier function. Results : Dental calculus induced dose-dependent cell death in HSC-2 cells, whereas cell death induced by freeze-dried bacteria was insignificant. Conversely, freeze-dried bacteria induced more cell death than dental calculus in THP-1 macrophages. Cell death induced by dental calculus but not by freeze-dried bacteria was inhibited by glyburide, indicating that these are different types of cell death. In the permeability assays, dental calculus but not freeze-dried bacteria attenuated the barrier function of HSC-2 cell monolayers. Conclusion : Due to the low sensitivity of HSC-2 cells to microbial cytotoxicity, dental calculus had stronger cytotoxic effects on HSC-2 cell monolayers than freeze-dried A. actinomycetemcomitans and F. nucleatum, suggesting that it plays a critical role in the breakdown of crevicular/pocket epithelium integrity. In the experiment, the researchers used many compounds, for example, 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8Synthetic Route of C23H28ClN3O5S).

5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide (cas: 10238-21-8) 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 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 C23H28ClN3O5S

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

Ionic (Co)Organocatalyst with (Thio)Urea Anion and Tetra-n-butyl Ammonium Cation for the Polymerization of γ-Butyrolactone was written by Ge, Fang;Wang, Zhe;Zhu, Yanyun;Wang, Xiaowu. And the article was included in Macromolecular Chemistry and Physics in 2020.Category: amides-buliding-blocks This article mentions the following:

An effective ionic organocatalyst system is developed for the challenging ring-opening polymerization (ROP) of γ-butyrolactone (GBL) at low temperature The catalysts are prepared by dehydration reaction between tetra-Bu ammonium hydroxide (TBAOH) and (thio)ureas at ambient temperature, and utilized with or without extra benzyl alc. (BnOH) initiator. The solid-state structure of TUA-3 comprising thiourea anion is characterized by X-ray diffraction anal. Typically, a mixture of cyclic and linear poly(GBL) with low mol. weights (5000-1600 g mol^-1) and slightly narrow mol. distribution ETH (1.2-1.4) is obtained by single base with/without combination with (thio)ureas. Interestingly, solely linear high-mol.-weight poly(GBL) (10 400 g mol^-1) can be achieved by a synergistic effect of TBAOH/N,N’-isopropylthiourea in the presence of BnOH. The obtained poly(GBL) is characterized with NMR spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDI-TOF MS). Mechanistic studies reveal different polymerization initiation steps in this reported catalyst system, which leads to poly(GBL) with divergent end groups. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Category: amides-buliding-blocks).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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. 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.Category: amides-buliding-blocks

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

Palladium-Catalyzed meta-Selective C-H Functionalization by Noncovalent H-Bonding Interaction was written by Li, Guoshuai;Yan, Yifei;Zhang, Pengfei;Xu, Xiaohua;Jin, Zhong. And the article was included in ACS Catalysis in 2021.Application of 2387-23-7 This article mentions the following:

Herein, a palladium-catalyzed meta-selective C-H olefination of aromatic carbonyl compounds such as acetophenone, benzaldehyde, Me benzoate, N,N-diisopropylbenzamide, etc. by noncovalent hydrogen-bonding interaction was reported. N,N’-Substituted ureas RNHC(O)NHR¹ [R = cyclohexyl, 3,5-bis(trifluoromethyl)phenyl; R¹ = cyclohexyl, 2-(2-cyanophenoxy)ethyl, 2-phenoxyethyl, etc.] were engineered to serve as a H-bonding donor for binding to the substrates and, meanwhile, achieve site-selective control by the integrated directing group. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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. 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 2387-23-7

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

Mn-Catalyzed Electrochemical Synthesis of Quinazolinones from Primary Alcohols/Benzyl Ethers and o-Aminobenzamides was written by Lin, Dian-Zhao;Lai, Yin-Long;Huang, Jing-Mei. And the article was included in ChemElectroChem in 2019.SDS of cas: 119023-25-5 This article mentions the following:

An efficient approach for the synthesis of quinazolinones I [R¹ = n-Bu, Ph, 3-pyridyl, etc.; R² = 4-Me, 3-OMe, 3-Br, etc; R³ = H, Me] from o-aminobenzamides and primary alcs./benzyl ethers using combination of electrochem. and redox-metal catalysis was developed. Taking manganese(II) sulfate as a redox catalyst, this transformation proceeded smoothly under ambient conditions in an undivided cell to afford I in moderate to excellent yields with a wide substrate scope. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5SDS of cas: 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 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.SDS of cas: 119023-25-5

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

Molecular and functional characterization of choline transporter-like proteins in esophageal cancer cells and potential therapeutic targets was written by Nagashima, Fumiaki;Nishiyama, Ryohta;Iwao, Beniko;Kawai, Yuiko;Ishii, Chikanao;Yamanaka, Tsuyoshi;Uchino, Hiroyuki;Inazu, Masato. And the article was included in Biomolecules & Therapeutics in 2018.Recommanded Product: 53902-12-8 This article mentions the following:

In this study, we examined the mol. and functional characterization of choline uptake in the human esophageal cancer cells. In addition, we examined the influence of various drugs on the transport of [3H]choline, and explored the possible correlation between the inhibition of choline uptake and apoptotic cell death. We found that both choline transporter-like protein 1 (CTL1) and CTL2 mRNAs and proteins were highly expressed in esophageal cancer cell lines (KYSE series). CTL1 and CTL2 were located in the plasma membrane and mitochondria, resp. Choline uptake was saturable and mediated by a single transport system, which is both Na+-independent and pH-dependent. Choline uptake and cell viability were inhibited by various cationic drugs. Furthermore, a correlation anal. of the potencies of 47 drugs for the inhibition of choline uptake and cell viability showed a strong correlation. Choline uptake inhibitors and choline deficiency each inhibited cell viability and increased caspase-3/7 activity. We conclude that extracellular choline is mainly transported via a CTL1. The functional inhibition of CTL1 by cationic drugs could promote apoptotic cell death. Furthermore, CTL2 may be involved in choline uptake in mitochondria, which is the rate-limiting step in S-adenosylmethionine (SAM) synthesis and DNA methylation. Identification of this CTL1- and CTL2-mediated choline transport system provides a potential new target for esophageal cancer therapy. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Recommanded Product: 53902-12-8).

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

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

Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes was written by Dale, Harvey J. A.;Nottingham, Chris;Poree, Carl;Lloyd-Jones, Guy C.. And the article was included in Journal of the American Chemical Society in 2021.Electric Literature of C10H10F3NO2 This article mentions the following:

Alkylidene carbenes undergo rapid inter- and intramol. reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of ¹³C-labeled precursors. Herein we report on the rearrangement of ¹³C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [¹³C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (¹³C{¹H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Electric Literature of C10H10F3NO2).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) 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 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 C10H10F3NO2

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

Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents was written by Yamazaki, Yuri;Sumikura, Makiko;Masuda, Yurika;Hayashi, Yoshiki;Yasui, Hiroyuki;Kiso, Yoshiaki;Chinen, Takumi;Usui, Takeo;Yakushiji, Fumika;Potts, Barbara;Neuteboom, Saskia;Palladino, Michael;Lloyd, George Kenneth;Hayashi, Yoshio. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Product Details of 116332-61-7 This article mentions the following:

KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC₅₀ value against HT-29 cells (IC₅₀ = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Product Details of 116332-61-7).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) 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. 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.Product Details of 116332-61-7

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