13820-14-9

Upstream product

• 85057-70-1 (Z)-3,4-dimethyl-5-<(4-methylphenyl)nitromethylene>-3-pyrrolin-2-one 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 36288-37-6 (Z)-N-hydroxy-4-methylbenzene-1-carbonimidoyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 36288-37-6 4-methylbenzohydroximoyl chloride 
• 29559-27-1 1-methyl-4-(nitromethyl)benzene 

Downstream Products

• 57984-77-7 (Z)-N'-hydroxy-4-methyl-N-phenylbenzimidamide 
• 57337-29-8 N-(3-p-tolyl-[1,4,2]oxathiazol-5-ylidene)-benzenesulfonamide 
• 13271-87-9 3-(p-tolyl)-5-acetoxy-4,5-dihydroisoxazole 
• 88611-56-7 5-ethylsulfanyl-3-p-tolyl-isoxazole 
• 5868-55-3 (3-p-tolyl-isoxazol-5-yl)-boronic acid 
• 71637-81-5 6a-methyl-3a,3b,7a-triphenyl-3,6-di-p-tolyl-(3ar,3br',6ac',7ac)-3a,3b,6a,7a-tetrahydro-cyclopenta[1,2-d;3,4-d']diisoxazol-7-one 
• 71637-75-7 3a-methyl-5,6,6a-triphenyl-3-p-tolyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 
• 71637-65-5 4-oxo-6,6a-diphenyl-3-p-tolyl-(6ac)-4,6a-dihydro-cyclopenta[d]isoxazol-3ar,5-dicarboxylic acid dimethyl ester 
• 71637-70-2 3a,5-diethyl-6,6a-diphenyl-3-p-tolyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 
• 71637-83-7 6a-ethyl-3a,3b,7a-triphenyl-3,6-di-p-tolyl-(3ar,3br',6ac',7ac)-3a,3b,6a,7a-tetrahydro-cyclopenta[1,2-d;3,4-d']diisoxazol-7-one 
• 54027-50-8 3-p-tolyl-3a,7b-dihydro-benzo[3,4]cyclobuta[1,2-d]isoxazole 
• 57750-30-8 8b-phenyl-3-p-tolyl-8bH-benzo[3,4]azeto[1,2-d][1,2,4]oxadiazole 
• 57750-20-6 2-phenyl-4-p-tolyl-benzo[1,3,5]oxadiazepine 
• 71637-60-0 3a,5,6,6a-tetraphenyl-3-p-tolyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 

Relevant academic research and scientific papers

Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin

A series of novel enantiomerically pure spiro-isoxazolidines and spiro-isoxazolines were synthesized regioselectively by 1,3-dipolar cycloaddition using respectively two dipoles, nitrones and nitrile oxides, on the exocyclic double bond of the B ring of t

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.

One-pot Synthesis of Some Novel Xanthine Derived Isoxazoles as Potent Antibacterial Agents

In search of better antibacterial agents, a series of novel xanthine derived 3,5-disubstituted isoxazole derivatives were synthesized (3a-3j) in one-pot using 8-chloro-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and aromatic aldehydes and f

Cu(I)-Catalysis of One-Pot Synthesis of Some Novel Regioselective Isoxazole-Benzimidazole Hybrids and Their In Vitro Anti-Cancer Evaluation

Regioselective synthesis of some novel isoxazole-benzimidazole hybrids in high yields via Cu(I)-catalyzed tandem one-pot reaction of aromatic aldehydes with 1-prop-2-ynylbenzimidazole is developed. Structures of the synthesized compounds are confirmed by

Hypervalent iodine-catalyzed cycloaddition of nitrile oxides to alkenes

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was fi

One-pot synthesis of isoxazolines from aldehydes catalyzed by iodobenzene

A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.

Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry

Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.

Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents

Several novel spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (α-methylene- γ-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of α,β-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described.

N-Heterocyclic carbene-catalyzed 1,3-dipolar cycloaddition reactions: A facile synthesis of 3,5-di- and 3,4,5-trisubstituted isoxazoles

A first example of organo-N-heterocyclic carbene (NHC) catalyzed click-type fast 1,3-dipolar cycloaddition of nitrile oxides with alkynes was developed for the regioselective synthesis of 3,5-di- and 3,4,5-trisubstituted isoxazoles. Triethylamine (Et