Tag: 200-300

《Derivatives of cinnamic acid interact with the nucleotide binding site of mitochondrial aldehyde dehydrogenase: effects on the dehydrogenase reaction and stimulation of esterase activity by nucleotides》 was written by Poole, Robert C.; Bowden, Nicola J.; Halestrap, Andrew P.. Reference of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide And the article was included in Biochemical Pharmacology on April 22 ,1993. The article conveys some information:

A wide variety of cinnamic acid derivatives are inhibitors of the low Km mitochondrial aldehyde dehydrogenase. Two of the most potent inhibitors are α-cyano-3,4-dihydroxythiocinnamamide (Ki 0.6 μM) and α-cyano-3,4,5-trihydroxycinnamonitrile (Ki 2.6 μM). With propionaldehyde as substrate the inhibition by these compounds was competitive with respect to NAD+. α-Fluorocinnamate was a much less effective inhibitor of the enzyme, with mixed behavior toward NAD+, but with a major competitive component. These cinnamic acid derivatives were ineffective as inhibitors of the aldehyde dehydrogenase-catalyzed hydrolysis of p-nitrophenyl acetate, but inhibited the ability of NAD+ and NADH to activate this activity. Inhibition of the stimulation of esterase activity was competitive with respect to NAD+ and NADH, and the derived Ki values were the same as for inhibition of dehydrogenase activity. NAD+, but not acetaldehyde, could elute the low Km aldehyde dehydrogenase from α-cyanocinnamate-Sepharose, to which the enzyme binds specifically. The cinnamic acid derivatives have little effect on lactate dehydrogenase, glyceraldehyde-3-phosphate dehydrogenase or a high Km aldehyde dehydrogenase present in rat liver mitochondria. Thus, some cinnamic acid derivatives are potent inhibitors of the low Km aldehyde dehydrogenase, by competing with NAD+/NADH for binding to the enzyme. They are much less effective as inhibitors of other NAD+-dependent dehydrogenases. The experimental part of the paper was very detailed, including the reaction process of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide(cas: 106392-48-7Reference of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide)

2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide(cas: 106392-48-7) 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.“,” In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Reference of 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide

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

In 2013,Urabe, Fumiya; Nagashima, Shunsuke; Takahashi, Keisuke; Ishihara, Jun; Hatakeyama, Susumi published 《Total Synthesis of (-)-Cinatrin C1 Based on an In(OTf)3-Catalyzed Conia-Ene Reaction》.Journal of Organic Chemistry published the findings.Application of 71432-55-8 The information in the text is summarized as follows:

The stereocontrolled total synthesis of (-)-cinatrin C1 (I), a phospholipase A2 inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted THF core by In(OTf)3-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester II followed by dihydroxylation with concomitant lactonization. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Application of 71432-55-8)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Application of 71432-55-8

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

Zhang, Wen; Wang, Xueyuan; Zhang, Haoyang; Wen, Tiantian; Yang, Lin; Miao, Hang; Wang, Jia; Liu, Hailong; Yang, Xu; Lei, Meng; Zhu, Yongqiang published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Discovery of novel tripeptide propylene oxide proteasome inhibitors for the treatment of multiple myeloma》.COA of Formula: C13H26N2O4 The author mentioned the following in the article:

The ubiquitin proteasome pathway (UPP) plays a critical role in the maintenance of cell homeostasis and the development of diseases, such as cancer and neurodegenerative disease. A series of novel tripeptide propylene oxide compounds as proteasome inhibitors were designed, synthesized and biol. investigated in this manuscript. The enzymic activities of final compounds against 20S human proteasome were investigated and structure-activity relationship (SAR) was summarized. Some potent compounds were further evaluated to inhibit the proliferation of multiple myeloma (MM) cancer cell lines RPMI8226 and U266B. The results showed that some compounds were active against MM cancer cell lines with IC50 values of less than 50 nM. The microsomal metabolic stabilities in human, rat and mice species were carried out and the results showed that compounds (I) (R1 = iso-Bu, Bn) were stable enough to be in vivo investigated. The in vivo pharmacokinetic results showed that compounds I (R1 = iso-Bu, Bn) had acceptable biol. parameters for both ig and iv administrations. In vivo antitumor activities of compounds I (R1 = iso-Bu, Bn) with the doses of 100 mg/kg and 50 mg/kg BIW were performed by using RPMI8226 xenograft nude mouse model. Toxicities of compounds I (R1 = iso-Bu, Bn) were not observed during the experiment and dose dependent effect was obvious and the tumor volume was greatly inhibited. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6COA of Formula: C13H26N2O4) was used in this study.

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.COA of Formula: C13H26N2O4Amides 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.

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

Lee, Min Jae; Bhattarai, Deepak; Jang, Hyeryung; Baek, Ahreum; Yeo, In Jun; Lee, Seongsoo; Miller, Zachary; Lee, Sukyeong; Hong, Jin Tae; Kim, Dong-Eun; Lee, Wooin; Kim, Kyung Bo published their research in Journal of Medicinal Chemistry on August 12 ,2021. The article was titled 《Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer’s Disease》.Category: amides-buliding-blocks The article contains the following contents:

Previously, we reported that immunoproteasome (iP)-targeting linear peptide epoxyketones improve cognitive function in mouse models of Alzheimer’s disease (AD) in a manner independent of amyloid β. However, these compounds’ clin. prospect for AD is limited due to potential issues, such as poor brain penetration and metabolic instability. Here, we report the development of iP-selective macrocyclic peptide epoxyketones prepared by a ring-closing metathesis reaction between two terminal alkenes attached at the P2 and P3/P4 positions of linear counterparts. We show that a lead macrocyclic compound DB-60 (20) effectively inhibits the catalytic activity of iP in ABCB1-overexpressing cells (IC50: 105 nM) and has metabolic stability superior to its linear counterpart. DB-60 (20) also lowered the serum levels of IL-1α and ameliorated cognitive deficits in Tg2576 mice. The results collectively suggest that macrocyclic peptide epoxyketones have improved CNS drug properties than their linear counterparts and offer promising potential as an AD drug candidate. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Category: amides-buliding-blocks)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Category: amides-buliding-blocksAmides 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.

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

《Copper(I)-mediated denitrogenative macrocyclization for the synthesis of cyclic α3β-tetrapeptide analogs》 was published in Chemistry – An Asian Journal in 2017. These research results belong to Chen, Chun-Chi; Wang, Sheng-Fu; Su, Yung-Yu; Lin, Yuya A.; Lin, Po-Chiao. Related Products of 87694-50-6 The article mentions the following:

A copper(I)-mediated denitrogenative reaction has been successfully developed for the preparation of cyclic tetrapeptides. The key reactive intermediate, ketenimine, triggers intramol. cyclization through attack of the terminal amine group to generate an internal β-amino acid with an amidine linkage. The chem. developed herein provides a new synthetic route for the preparation of cyclic α3β-tetrapeptide analogs that contain important biol. properties and results in rich structural information being obtained for conformational studies. With the success of this copper(I)-catalyzed macrocyclization, two histone deacetylase inhibitor analogs consisting of the cyclic α3β-tetrapeptide framework have been successfully synthesized. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Related Products of 87694-50-6) was used in this study.

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Related Products of 87694-50-6 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.

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

《An easy and convenient synthesis of Weinreb amides and hydroxamates》 was written by de Luca, Lidia; Giacomelli, Giampaolo; Taddei, Maurizio. Synthetic Route of C13H26N2O4 And the article was included in Journal of Organic Chemistry on April 6 ,2001. The article conveys some information:

A simple and convenient one-flask method for the preparation of Weinreb amides, hydroxamates, and hydroxamic acids on a large scale used mild reaction conditions and inexpensive reagents; the methodol. is a useful addition to parallel syntheses. Thus, reacting PhCO2H with MeNHOMe in THF containing 2-chloro-4,6-dimethoxy-1,3,5-triazine [CMDT], 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride [DMTMM], or cyanuric chloride and N-methylmorpholine [NMM] gave the amide PhCONMeOMe in high yields. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Synthetic Route of C13H26N2O4 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.

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

Sheng, Yuwen; Chen, Yuwen; Zeng, Zhongqiu; Wu, Wenbi; Wang, Jing; Ma, Yuling; Lin, Yuan; Zhang, Jichao; Huang, Yulan; Li, Wenhua; Zhu, Qiyu; Wei, Xiao; Li, Suiyan; Wisanwattana, Wisanee; Li, Fu; Liu, Wanli; Suksamrarn, Apichart; Zhang, Guolin; Jiao, Wei; Wang, Fei published an article on January 13 ,2022. The article was titled 《Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming》, and you may find the article in Journal of Medicinal Chemistry.Synthetic Route of C11H22N2O4 The information in the text is summarized as follows:

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chem.-based probe strategy. Erianin potently inhibited the enzymic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Anal. of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC. The results came from multiple reactions, including the reaction of H-Lys(Boc)-OH(cas: 2418-95-3Synthetic Route of C11H22N2O4)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. In addition to subunits of proteins, amino acids have many other functions as well, including osmoregulation (proline), neurotransmitters (gamma-aminobutyric acid), metabolic intermediates (ornithine and citrulline), and inhibitors (dehydroproline).Synthetic Route of C11H22N2O4

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

Kaloudi, Aikaterini; Kanellopoulos, Panagiotis; Radolf, Thorsten; Chepurny, Oleg G.; Rouchota, Maritina; Loudos, George; Andreae, Fritz; Holz, George G.; Nock, Berthold Artur; Maina, Theodosia published their research in Molecular Pharmaceutics on August 3 ,2020. The article was titled 《[99mTc]Tc-DGA1, a Promising CCK2R-Antagonist-Based Tracer for Tumor Diagnosis with Single-Photon Emission Computed Tomography》.Reference of H-Lys(Boc)-OH The article contains the following contents:

Radiolabeled gastrin analogs have been proposed for theranostics of cholecystokinin subtype 2 receptor (CCK2R)-pos. cancer. Peptide radioligands based on other receptor antagonists have displayed superior pharmacokinetics and higher biosafety than agonists. Here, we present DGA1, a derivative of the nonpeptidic CCK2R antagonist Z-360 carrying an acyclic tetraamine, for [99mTc]Tc labeling. Preclin. comparison of [99mTc]Tc-DGA1 with [99mTc]Tc-DG2 (CCK2R-agonist reference) was conducted in HEK293-CCK2R/CCK2i4svR cells and mice models, qualifying [99mTc]Tc-DGA1 for further study in patients with CCK2R-pos. tumors and single-photon emission computed tomog./CT. In the experiment, the researchers used H-Lys(Boc)-OH(cas: 2418-95-3Reference of H-Lys(Boc)-OH)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. In addition to subunits of proteins, amino acids have many other functions as well, including osmoregulation (proline), neurotransmitters (gamma-aminobutyric acid), metabolic intermediates (ornithine and citrulline), and inhibitors (dehydroproline).Reference of H-Lys(Boc)-OH

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

In 2020,Advanced Functional Materials included an article by Feng, Jiale; Yang, Lupeng; Romanov, Alexander S.; Ratanapreechachai, Jirawit; Reponen, Antti-Pekka M.; Jones, Saul T. E.; Linnolahti, Mikko; Hele, Timothy J. H.; Koehler, Anna; Baessler, Heinz; Bochmann, Manfred; Credgington, Dan. Quality Control of N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide. The article was titled 《Environmental Control of Triplet Emission in Donor-Bridge-Acceptor Organometallics》. The information in the text is summarized as follows:

Carbene-metal-amides (CMAs) are a promising family of donor-bridge-acceptor mol. charge-transfer (CT) emitters for organic light-emitting diodes. A universal approach is demonstrated to tune the energy of their CT emission. A blueshift of ≤210 meV is achievable in solid state via dilution in a polar host matrix. The origin of this shift has 2 components: constraint of thermally-activated triplet diffusion, and electrostatic interactions between guest and polar host. This allows the emission of mid-green CMA archetypes to be tuned to sky blue without chem. modifications. Monte-Carlo simulations based on a Marcus-type transfer integral reproduce the concentration- and temperature-dependent triplet diffusion process, revealing a substantial shift in the ensemble d. of states in polar hosts. In Au-bridged CMAs, this shift does not lead to a significant change in luminescence lifetime, thermal activation energy, reorganization energy, or intersystem crossing rate. These discoveries offer new insight into coupling between the singlet and triplet manifolds in CMA materials, revealing a dominant interaction between states of CT character. The same approach is employed using materials which were chem. modified to alter the energy of their CT state directly, shifting the emission of sky-blue chromophores into the practical blue range. In the experiment, the researchers used N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide(cas: 247170-19-0Quality Control of N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide)

N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide(cas: 247170-19-0) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Quality Control of N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide

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

Formula: C13H26N2O4On September 15, 2019 ,《Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors》 was published in Bioorganic & Medicinal Chemistry. The article was written by Lei, Meng; Zhang, Haoyang; Miao, Hang; Du, Xiao; Zhou, Hui; Wang, Jia; Wang, Xueyuan; Feng, Huayun; Shi, Jingmiao; Liu, Zhaogang; Shen, Jian; Zhu, Yongqiang. The article contains the following contents:

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biol. assayed. Based on the enzymic results, seven compounds were selected to evaluate their cellular activities and soluble compound (I) showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound I was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, resp. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound I and carfilzomib was carried out. The results indicated that I had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM. The experimental part of the paper was very detailed, including the reaction process of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Formula: C13H26N2O4 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.

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