October 2022 - Page 87 of 127 - Amides-buliding-blocks

Gonnet, Lori’s team published research in Angewandte Chemie, International Edition in 2022-03-21 | 94-20-2

Angewandte Chemie, International Edition published new progress about Antidiabetic agents. 94-20-2 belongs to class amides-buliding-blocks, and the molecular formula is C10H13ClN2O3S, Application of C10H13ClN2O3S.

Gonnet, Lori; Lennox, Cameron B.; Do, Jean-Louis; Malvestiti, Ivani; Koenig, Stefan G.; Nagapudi, Karthik; Friscic, Tomislav published the artcile< Metal-Catalyzed Organic Reactions by Resonant Acoustic Mixing>, Application of C10H13ClN2O3S, the main research area is tolbutamide preparation antidiabetic; Acoustic Mixing; Catalysis; Green Chemistry; Mechanochemistry; Pharmaceuticals.

Catalytic organic synthesis by resonant acoustic mixing (RAM), a mechanochem. methodol. that does not require bulk solvent or milling media. Using as model reactions ruthenium-catalyzed ring-closing metathesis and copper-catalyzed sulfonamide-isocyanate coupling, RAM mechanosynthesis was shown to be faster, operationally simpler than conventional ball-milling, while also provided the first example of a mechanochem. strategy for ruthenium-catalyzed ene-yne metathesis. Reactions by RAM were readily and directly scaled-up without any significant changes in reaction conditions, as shown by the straightforward 200-fold scaling-up of the synthesis of the antidiabetic drug Tolbutamide, from hundreds of milligrams directly to 30 g.

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

Shi, Zhi-Bing’s team published research in Chemical & Pharmaceutical Bulletin in 2012-12-31 | 1524-40-9

Chemical & Pharmaceutical Bulletin published new progress about Animal oncogene Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Electric Literature of 1524-40-9.

Shi, Zhi-Bing; Zhao, Dan; Huang, Yan-Yan; Du, Yun; Cao, Xiang-Rong; Gong, Zhu-Nan; Zhao, Rui; Li, Jian-Xin published the artcile< Discovery, synthesis, and evaluation of small-molecule signal transducer and activator of transcription 3 inhibitors>, Electric Literature of 1524-40-9, the main research area is transcription factor STAT3 inhibitor anticancer antitumor benzoxazole benzenesulfonamide.

The signal transducer and activator of transcription 3 (STAT3) oncogene is a promising mol. target and its inhibitors have great potential as anticancer drugs. To identify novel and STAT3-selective inhibitors, a virtual screening based on Specs and Maybridge databases was conducted and a 6,6′-bibenzoxazole type small mol. with an inhibition constant Ki value of 494.32 nm to STAT3 was explored. Further, a novel series of compounds was synthesized and evaluated by a cell-based assay using human breast cancer cell lines, MDA-MB-468 and MCF-7 with or without constitutive expression of STAT3, resp. Several compounds displayed inhibitory activity and good selectivity. Several compounds also significantly inhibited STAT3 protein level and also displayed binding affinity for STAT3 that detected with flow injection anal.-quartz crystal microbalance (FIA-QCM) anal. system. The results provided a new lead for future design and development of potent STAT3 inhibitors. The synthesis of the target compounds was achieved using 4,4′-diamino-[1,1′-biphenyl]-3,3′-diol (3,3′-dihydroxybenzidine) as a starting material. The title compounds thus formed included N,N’-[6,6′-bibenzoxazole]-2,2′-diylbis[benzenesulfonamide] (I) and related substances, such asN-(2-benzoxazolyl)-2-methylbenzenesulfonamide.

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

Patil, Nitin T’s team published research in Journal of Organic Chemistry in 2010-02-19 | 5004-88-6

Journal of Organic Chemistry published new progress about Alkynyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 5004-88-6 belongs to class amides-buliding-blocks, and the molecular formula is C9H12N2O3, Application of C9H12N2O3.

Patil, Nitin T.; Kavthe, Rahul D.; Raut, Vivek S.; Shinde, Valmik S.; Sridhar, Balasubramanian published the artcile< Gold- and Platinum-Catalyzed Formal Markownikoff's Double Hydroamination of Alkynes: A Rapid Access to Tetrahydroquinazolinones and Angularly-Fused Analogues Thereof>, Application of C9H12N2O3, the main research area is alkynol aminobenzamide gold platinum Markownikoff hydroamination; tetrahydroquinazolinone preparation; angularly fused hexahydropyrroloquinazolinone preparation; Markownikoff hydroamination catalyst gold platinum.

A highly efficient gold(I)- and platinum(II)-catalyzed process for formal Markownikoff’s double hydroamination of alkynes tethered with hydroxyl group has been developed. The method was shown to be applicable to a broad range of 2-aminobenzamides and alkynols leading to the formation of multiply substituted tetrahydroquinazolinones. Interestingly, when Pt(IV)Cl4 catalyst was employed, cyclic angularly fused compound was obtained.

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

Lai, Kuo-Chu’s team published research in Anticancer Research in 2021-01-31 | 5004-88-6

Anticancer Research published new progress about Antitumor agents. 5004-88-6 belongs to class amides-buliding-blocks, and the molecular formula is C9H12N2O3, Name: 2-Amino-4,5-dimethoxybenzamide.

Lai, Kuo-Chu; Chia, Yi-Ting; Yih, Ling-Huei; Lu, Yi-Liang; Chang, Shih-Ting; Hong, Zi-Xuan; Chen, Tai-Lin; Hour, Mann-Jen published the artcile< Antitumor effects of the novel quinazolinone Holu-12: induction of mitotic arrest and apoptosis in human oral squamous cell carcinoma CAL27 cells>, Name: 2-Amino-4,5-dimethoxybenzamide, the main research area is quinazolinone mitotic arrest human oral squamous cell carcinoma apoptosis; 5-FU sensitivity; Quinazolinone derivatives; apoptosis; human oral squamous cell carcinoma; mitotic arrest.

Quinazolinone is a privileged chem. structure employed for targeting various types of cancer. This study aimed to demonstrate the antitumor activity of synthesized 6,7-disubstituted-2-(3-fluorophenyl) quinazolines (HoLu-11 to HoLu-14). The cytotoxicity was assessed by the sulforhodamine B (SRB) assay. The cell cycle was examined by flow cytometry. The expression levels of cell cycle- and apoptosis-related proteins were estimated by western blotting. A xenograft animal model was used to explore the antitumor effects of HoLu-12. Among four synthetic quinazolinone derivatives, HoLu-12 significantly reduced the viability of oral squamous cell carcinoma (OSCC) cells. HoLu-12 induced G2/M arrest and increased the expression of cyclin B, histone H3 (Ser10) phosphorylation, and cleaved PARP, indicating that HoLu-12 could induce mitotic arrest and then apoptosis. Moreover, the combination of HoLu-12 and 5-fluorouracil (5-FU) displayed synergistic toxic effect on OSCC cells. HoLu-12 significantly inhibited tumor growth in vivo. HoLu-12 induces mitotic arrest and leads to apoptosis of OSCC cells. Furthermore, HoLu-12 alone or in combination with 5-FU is a potential therapeutic agent for OSCC.

Anticancer Research published new progress about Antitumor agents. 5004-88-6 belongs to class amides-buliding-blocks, and the molecular formula is C9H12N2O3, Name: 2-Amino-4,5-dimethoxybenzamide.

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

Lai, Nanjun’s team published research in Frontiers in Chemistry (Lausanne, Switzerland) in 2020 | CAS: 70-55-3

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.HPLC of Formula: 70-55-3

《CO2/N2-responsive nanoparticles for enhanced oil recovery during CO2 flooding》 was published in Frontiers in Chemistry (Lausanne, Switzerland) in 2020. These research results belong to Lai, Nanjun; Zhu, Qingru; Qiao, Dongyu; Chen, Ke; Wang, Dongdong; Tang, Lei; Chen, Gang. HPLC of Formula: 70-55-3 The article mentions the following:

During CO2 flooding, serious gas channeling occurs in ultra-low permeability reservoirs due to the high mobility of CO2. The chief end of this work was to research the application of responsive nanoparticles for mobility control to enhance oil recovery. Responsive nanoparticles were developed based on the modification of nano-silica (SiO2) by 3-aminopropyltrimethoxysilane (KH540) via the Eschweiler-Clark reaction. The proof of concept for responsive nanoparticles was investigated by FT-IR, 1H-NMR, TEM, DLS, CO2/N2 response, wettability, plugging performance, and core flooding experiments The results indicated that responsive nanoparticles exhibited a good response to control nanoparticle dispersity due to electrostatic interaction. Subsequently, responsive nanoparticles showed a better plugging capacity of 93.3% to control CO2 mobility, and more than 26% of the original oil was recovered. Moreover, the proposed responsive nanoparticles could revert oil-wet surfaces to water-wet, depending on surface adsorption to remove the oil fromthe surface of the rocks. The results of this work indicated that responsive nanoparticles might have potential applications for improved oil recovery in ultra-low permeability reservoirs. The results came from multiple reactions, including the reaction of 4-Methylbenzenesulfonamide(cas: 70-55-3HPLC of Formula: 70-55-3)

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

Tan, Guangying’s team published research in Angewandte Chemie, International Edition in 2021 | CAS: 78191-00-1

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.COA of Formula: C4H9NO2

Tan, Guangying; Das, Mowpriya; Maisuls, Ivan; Strassert, Cristian A.; Glorius, Frank published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Rhodium-Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds》.COA of Formula: C4H9NO2 The article contains the following contents:

Herein, the first example of rhodium-catalyzed dealkenylative arylation of alkenes with arylboronic compounds, thereby providing an unconventional access to biaryls with excellent chemoselectivity was diclosed. In this method, C(aryl)-C(alkenyl) and C(alkenyl)-C(alkenyl) bonds in various alkenes and 1,3-dienes could be cleaved via a hydrometalation and followed by β-carbon elimination pathway for Suzuki-Miyaura reactions. Furthermore, a series of novel organic fluorescent mols. with excellent photophys. properties were efficiently constructed with this protocol. The experimental part of the paper was very detailed, including the reaction process of N-Methoxy-N-methylacetamide(cas: 78191-00-1COA of Formula: C4H9NO2)

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

Zhang, Nanping’s team published research in Angewandte Chemie, International Edition in 2022 | CAS: 78191-00-1

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Electric Literature of C4H9NO2

In 2022,Zhang, Nanping; Jiang, Huanfeng; Ma, Zhiqiang published an article in Angewandte Chemie, International Edition. The title of the article was 《Concise Synthesis of (±)-Myrioneurinol Enabled by Sequential [2+2] Cycloaddition/Retro-Mannich Fragmentation/Mannich Reaction》.Electric Literature of C4H9NO2 The author mentioned the following in the article:

A concise total synthesis of (±)-myrioneurinol has been achieved in 14 steps. An efficient AgSbF6/t-BuCl-catalyzed intramol. [2+2] cycloaddition reaction of the alkynone-tethered enamine was developed to prepare the highly strained cyclobutene. It was used in combination with a subsequent retro-Mannich fragmentation/Mannich reaction to efficiently construct the tricyclic core of myrioneurinol. After reading the article, we found that the author used N-Methoxy-N-methylacetamide(cas: 78191-00-1Electric Literature of C4H9NO2)

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

Zabala, Daniel’s team published research in Journal of the American Chemical Society in 2016 | CAS: 87694-50-6

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

《A Flavin-Dependent Decarboxylase-Dehydrogenase-Monooxygenase Assembles the Warhead of α,β-Epoxyketone Proteasome Inhibitors》 was written by Zabala, Daniel; Cartwright, Joshua W.; Roberts, Douglas M.; Law, Brian J. C.; Song, Lijiang; Samborskyy, Markiyan; Leadlay, Peter F.; Micklefield, Jason; Challis, Gregory L.. Computed Properties of C13H26N2O4 And the article was included in Journal of the American Chemical Society on April 6 ,2016. The article conveys some information:

The α,β-epoxyketone proteasome inhibitor TMC-86A was discovered as a previously unreported metabolite of Streptomyces chromofuscus ATCC49982, and the gene cluster responsible for its biosynthesis was identified via genome sequencing. Incorporation experiments with [13C-methyl]L-methionine implicated an α-dimethyl-β-keto acid intermediate in the biosynthesis of TMC-86A. Incubation of the chem. synthesized α-dimethyl-β-keto acid with a purified recombinant flavin-dependent enzyme that is conserved in all known pathways for epoxyketone biosynthesis resulted in formation of the corresponding α-methyl-α,β-epoxyketone. This transformation appears to proceed via an unprecedented decarboxylation-dehydrogenation-monooxygenation cascade. The biosynthesis of the TMC-86A warhead is completed by cytochrome P 450-mediated hydroxylation of the α-methyl-α,β-epoxyketone. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Computed Properties of C13H26N2O4)

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

Dornan, Peter K.’s team published research in Organic Process Research & Development in 2020 | CAS: 87694-50-6

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

《Continuous process improvement in the manufacture of carfilzomib. Part 1: Process understanding and improvements in the commercial route to prepare the epoxyketone warhead》 was written by Dornan, Peter K.; Anthoine, Travis; Beaver, Matthew G.; Cheng, Guilong Charles; Cohen, Dawn E.; Cui, Sheng; Lake, William E.; Langille, Neil F.; Lucas, Susan P.; Patel, Jenil; Powazinik, William; Roberts, Scott W.; Scardino, Chris; Tucker, John L.; Spada, Simone; Zeng, Alicia; Walker, Shawn D.. Formula: C13H26N2O4 And the article was included in Organic Process Research & Development on April 17 ,2020. The article conveys some information:

In the first case study, the mechanism of racemization of an α-chiral enone was investigated, resulting in the development of an improved aqueous workup procedure. Next, the stability of a bleach/pyridine mixture used for the step 3 epoxidation reaction was studied, leading to the identification of pyridine as a key raw material and improved reaction conditions and control strategy to meet the conversion target. Finally, oxidized butylated hydroxytoluene (oBHT) was identified as an impurity arising from the use of BHT-stabilized THF in steps preceding the oxidation The process understanding obtained from these investigations have led to the implementation of process improvements which improve the robustness of the process. The development of a second-generation route to epoxyketone I was the subject of the second manuscript in this series. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

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

Ghosh, Arun K.’s team published research in Journal of the American Chemical Society in 2000 | CAS: 87694-50-6

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) 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 (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

《Design of potent inhibitors for human brain memapsin 2 (β-secretase)》 was written by Ghosh, Arun K.; Shin, Dongwoo; Downs, Debbie; Koelsch, Gerald; Lin, Xinli; Ermolieff, Jacques; Tang, Jordan. Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide And the article was included in Journal of the American Chemical Society on April 12 ,2000. The article conveys some information:

Two highly potent inhibitors of human memapsin 2 were designed and synthesized from current available specificity information. The inhibitors, OM99-1 and OM99-2, were tested for inhibition of recombinant human memapsin 2 prepared from E. coli expression. In the part of experimental materials, we found many familiar compounds, such as (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)

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