Tag: M.W=150-200

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

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.

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.

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

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.

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.

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

Zhu, Yan-ping; Fei, Zhuan; Liu, Mei-cai; Jia, Feng-cheng; Wu, An-xin published the artcile< Direct One-Pot Synthesis of Luotonin F and Analogues via Rational Logical Design>, Application of C9H12N2O3, the main research area is luotonin F synthesis iodination Kornblum oxidation annulation; quinazolinone acyl derivative preparation.

An efficient one-pot synthetic protocol has been proposed for the synthesis of luotonin F [2-(3-quinolinylcarbonyl)-4(1H)-quinazolinone] from easily available starting materials. Through a rational logical design, multifundamental reactions (iodination, Kornblum oxidation, and annulation) were assembled in one-pot. The developed approach can efficiently synthesize luotonin F and a diversity of analogs.

Organic Letters published new progress about Cyclization. 5004-88-6 belongs to class amides-buliding-blocks, and the molecular formula is C9H12N2O3, Application of C9H12N2O3.

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

Althuis, T. H.; Moore, P. F.; Hess, H. J. published the artcile< Development of ethyl 3,4-dihydro-4-oxopyrimido[4,5-b]quinoline-2-carboxylate, a new prototype with oral antiallergy activity>, Formula: C9H12N2O3, the main research area is quinazolinecarboxylate analog preparation antiallergic; allergy inhibitor quinazolinecarboxylate analog; cromoglycate analog allergy inhibitor.

The synthesis and antiallergic activity is described of 18 3,4-dihydro-4-oxoquinazoline-2-carboxylic acid analogs I (R = H, MeO, NO2, Br, etc.; R1 = H or Et; X = CH or N) and II (R = H, CO2Na, CO2Et, OH, etc.; X = CH or N). The title compound II (R = CO2Et, X = N) [55149-04-7] was 10 times more potent (ED50 = 3 mg/kg, orally) than di-Na cromoglycate in the rat passive cutaneous anaphylaxis test. Structure-activity relations are discussed.

Journal of Medicinal Chemistry published new progress about Allergy. 5004-88-6 belongs to class amides-buliding-blocks, and the molecular formula is C9H12N2O3, Formula: C9H12N2O3.

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

Zhou, Jie; Bie, Jianbo; Wang, Xiaoyu; Liu, Quan; Li, Rongcui; Chen, Hualong; Hu, Jinping; Cao, Hui; Ji, Wenming; Li, Yan; Liu, Shuainan; Shen, Zhufang; Xu, Bailing published the artcile< Discovery of N-Arylsulfonyl-Indole-2-Carboxamide Derivatives as Potent, Selective, and Orally Bioavailable Fructose-1,6-Bisphosphatase Inhibitors-Design, Synthesis, In Vivo Glucose Lowering Effects, and X-ray Crystal Complex Analysis>, Application of C6H6FNO2S, the main research area is T2MD liver FBPase inhibitors glucose lowering crystal structure binding.

Liver fructose-1,6-bisphosphatase (FBPase) is a key enzyme in the gluconeogenesis pathway. Inhibiting FBPase activity represents a potential treatment for type 2 diabetes mellitus. A series of novel N-arylsulfonyl-4-arylamino-indole-2-carboxamide derivatives have been disclosed as FBPase inhibitors. Through extensive structure-activity relationship investigations, a promising candidate mol. Cpd118 [sodium (7-chloro-4-((3-methoxyphenyl)amino)-1-methyl-1H-indole-2-carbonyl] [(4-methoxyphenyl)sulfonyl)amide](I) has been identified with high inhibitory activity against human liver FBPase (IC50, 0.029 ± 0.006 μM) and high selectivity relative to the other six AMP-binding enzymes. Importantly, Cpd118 produced significant glucose-lowering effects on both type 2 diabetic KKAy mice and ZDF rats as demonstrated by substantial reductions in the fasting and postprandial blood glucose levels, as well as the HbA1c level. Furthermore, Cpd118 elicited a favorable pharmacokinetic profile with an oral bioavailability of 99.1%. Moreover, the X-ray crystal structure of the Cpd118-FBPase complex was resolved, which revealed a unique binding mode and provided a structural basis for its high potency and selectivity.

Journal of Medicinal Chemistry published new progress about Bioavailability. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Application of C6H6FNO2S.

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

Lee, Seohoo; Sim, Jaeuk; Jo, Hyeju; Viji, Mayavan; Srinu, Lanka; Lee, Kiho; Lee, Heesoon; Manjunatha, Vishwanath; Jung, Jae-Kyung published the artcile< Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon>, HPLC of Formula: 5004-88-6, the main research area is quinazolinone preparation transition metal free microwave irradiation; dimethyl sulfoxide aminobenzamide intramol oxidative annulation.

Biol. important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramol. oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by this methodol. The present method involves the synthesis of quinazolinones with a broad substrate scope and a good yield.

Organic & Biomolecular Chemistry published new progress about Benzamides Role: RCT (Reactant), RACT (Reactant or Reagent) (amino). 5004-88-6 belongs to class amides-buliding-blocks, and the molecular formula is C9H12N2O3, HPLC of Formula: 5004-88-6.

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

Jiang, Yutong; Andrews, Steven W.; Condroski, Kevin R.; Buckman, Brad; Serebryany, Vlad; Wenglowsky, Steve; Kennedy, April L.; Madduru, Machender R.; Wang, Bin; Lyon, Michael; Doherty, George A.; Woodard, Benjamin T.; Lemieux, Christine; Do, Mary Geck; Zhang, Hailong; Ballard, Joshua; Vigers, Guy; Brandhuber, Barbra J.; Stengel, Peter; Josey, John A.; Beigelman, Leonid; Blatt, Lawrence; Seiwert, Scott D. published the artcile< Discovery of Danoprevir (ITMN-191/R7227), a Highly Selective and Potent Inhibitor of Hepatitis C Virus (HCV) NS3/4A Protease>, Safety of Morpholine-4-sulfonamide, the main research area is danoprevir macrocyclic peptidomimetic acylsulfonamide preparation inhibitor HCV NS3 protease.

HCV serine protease NS3 represents an attractive drug target because it is not only essential for viral replication but also implicated in the viral evasion of the host immune response pathway through direct cleavage of key proteins in the human innate immune system. Through structure-based drug design and optimization, macrocyclic peptidomimetic mols. bearing both a lipophilic P2 isoindoline carbamate and a P1/P1′ acylsulfonamide/acylsulfamide carboxylic acid bioisostere were prepared that possessed subnanomolar potency against the NS3 protease in a subgenomic replicon-based cellular assay (Huh-7). Danoprevir (compound 49) was selected as the clin. development candidate for its favorable potency profile across multiple HCV genotypes and key mutant strains and for its good in vitro ADME profiles and in vivo target tissue (liver) exposures across multiple animal species. X-ray crystallog. studies elucidated several key features in the binding of danoprevir to HCV NS3 protease and proved invaluable to the iterative structure-based design strategy of the authors.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 25999-04-6 belongs to class amides-buliding-blocks, and the molecular formula is C4H10N2O3S, Safety of Morpholine-4-sulfonamide.

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

Nishad, Chandra Shekhar; Haldar, Krishna Kanta; Banerjee, Biplab published the artcile< Metal-Free Direct Access to N-Sulfonyl Amidines from Sulfonamides and Secondary Amines Involving Tandem C-N Bond Formations>, Recommanded Product: 3-Fluorobenzenesulfonamide, the main research area is sulfonyl amidine preparation metal free one pot; sulfonamide secondary amine tandem carbon nitrogen bond formation.

Authors report a mild and efficient metal-free one-pot procedure for the synthesis of N-sulfonyl amidines via the direct reaction of sulfonamides with secondary amines without using any additives. A wide range of substrates with variety of functional groups is well tolerated under the reaction conditions. Preliminary mechanistic studies indicate that the secondary amine plays a dual role as a C1 source of the amidine group and an aminating agent. Synthetic utility of this method is shown in the late-stage functionalization of drug mols. on the gram scale.

Journal of Organic Chemistry published new progress about Alicyclic amines Role: RCT (Reactant), RACT (Reactant or Reagent). 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Recommanded Product: 3-Fluorobenzenesulfonamide.

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

Liu, Peng; Chen, Xiaozhong; Xu, Xiangchao; Yang, Linlin; Zeng, Guixiang; Ye, Chuang; Shi, Qixun; Yang, Jiazhi; Li, Feng published the artcile< From hydrogen autotransfer process to deuterium autotransfer process: The N-trideuteromethylation of amines with deuterated methanol to trideuteromethylated amines catalyzed by a Cp*Ir complex bearing a flexible bridging and functional ligand>, Category: amides-buliding-blocks, the main research area is perdeuteromethanol amine iridium catalyst trideuteromethylation green chem; trideuteromethylamine preparation; sulfonamide perdeuteromethanol iridium catalyst trideuteromethylation green chem; trideuterosulfonamide preparation.

A Cp*Ir complex bearing a flexible and functional 6,6′-(OH)2-2,2′-dipyridylamine ligand was designed, synthesized and found to be a general and efficient catalyst for the synthesis of trideuteromethylated amines via the N-trideuteromethylation of amines with deuterated methanol based on the proposed deuterium autotransfer process. The synthetic strategy was attractive due to easily available deuterium source, high atom efficiency and environmental friendliness. It was confirmed that OH units in the ligand were crucial for the catalytic activity. Furthermore, a metal-ligand cooperative mechanism was also proposed based on exptl. results and DFT calculations

Journal of Catalysis published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6961-82-6 belongs to class amides-buliding-blocks, and the molecular formula is C6H6ClNO2S, Category: amides-buliding-blocks.

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