Category: isoxazole

Selective CB2 receptor agonists. Part 3: The optimization of a piperidine-based series that demonstrated efficacy in an in vivo neuropathic pain model was written by Bartolozzi, Alessandra;Cirillo, Pier Francesco;Berry, Angela K.;Hickey, Eugene R.;Thomson, David S.;Wu, Lifen;Zindell, Renee;Albrecht, Claudia;Ceci, Angelo;Gemkow, Mark J.;Nagaraja, Nelamangala V.;Romig, Helmut;Sauer, Achim;Riether, Doris. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Category: isoxazole This article mentions the following:

A novel class of potent cannabinoid receptor 2 (CB2) agonists based on a (S)-piperidine scaffold was identified using ligand-based pharmacophore models. Optimization of solubility and metabolic stability led to the identification of several potent CB2 agonists, e.g. I, that displayed selectivity over cannabinoid receptor 1 (CB1) and acceptable drug like properties. In rats, compound 30 demonstrated a favorable pharmacokinetic profile and efficacy in a Streptozotocin-induced diabetic neuropathy model, with full reversal of mech. hyperalgesia. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Category: isoxazole).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazole rings are found in some natural products, such as ibotenic acid and muscimol. The most common methods for N–O bond cleavage in isoxazoles are hydrogenation with palladium or platinum catalysts or with Raney Ni. Recent developments have shown that Mo(CO)6 efficiently cleaves the N–O bond in isoxazoles.Category: isoxazole

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Selective CB2 receptor agonists. Part 2: Structure-activity relationship studies and optimization of proline-based compounds was written by Riether, Doris;Zindell, Renee;Wu, Lifen;Betageri, Raj;Jenkins, James E.;Khor, Someina;Berry, Angela K.;Hickey, Eugene R.;Ermann, Monika;Albrecht, Claudia;Ceci, Angelo;Gemkow, Mark J.;Nagaraja, Nelamangala V.;Romig, Helmut;Sauer, Achim;Thomson, David S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Safety of 3-(tert-Butyl)isoxazol-5-amine This article mentions the following:

Through a ligand-based pharmacophore model (S)-proline based compounds were identified as potent cannabinoid receptor 2 (CB2) agonists with high selectivity over the cannabinoid receptor 1 (CB1). Structure-activity relationship investigations for this compound class lead to oxo-proline compounds I and II which combine an impressive CB1 selectivity profile with good pharmacokinetic properties. In a streptozotocin induced diabetic neuropathy model, II demonstrated a dose-dependent reversal of mech. hyperalgesia. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Safety of 3-(tert-Butyl)isoxazol-5-amine).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles present in various natural products and synthetic compounds of biological importance like antibacterial, antagonists, antiinflammatory, analgesics, and also show the applications in functional materials. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Safety of 3-(tert-Butyl)isoxazol-5-amine

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Synthesis and biological evaluation of chromenylurea and chromanylurea derivatives as anti-TNF-α agents that target the p38 MAPK pathway was written by Li, Xingzhou;Zhou, Xinming;Zhang, Jing;Wang, Lili;Long, Long;Zheng, Zhibing;Li, Song;Zhong, Wu. And the article was included in Molecules in 2014.Quality Control of 3-(tert-Butyl)isoxazol-5-amine This article mentions the following:

A series of 1-aryl-3-(2H-chromen-5-yl)urea I (R¹ = H, 3-Me, 4-Me) and 1-aryl-3-(chroman-5-yl)urea derivatives II (R¹ = 4-Me, 4-F, 4-Cl, etc.) were designed, synthesized and evaluated for their inhibitory activities towards TNF-α production in lipopolysaccharide-stimulated THP-1 cells. The most active compound, II (R¹ = 4-NO₂) inhibited TNF-α release with an IC₅₀ value of 0.033 μM, which is equipotent to that of BIRB796 (IC₅₀ = 0.032 μM). In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Quality Control of 3-(tert-Butyl)isoxazol-5-amine).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Quality Control of 3-(tert-Butyl)isoxazol-5-amine

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

An efficient synthesis of fused 3-formylpyridines and 5-formylpyrimidines was written by Mityuk, Andrey P.;Kolodych, Sergey E.;Mytnyk, Sergey A.;Dmytriv, Yuri V.;Volochnyuk, Dmitriy M.;Mykhailiuk, Pavel K.;Tolmachev, Andrey A.. And the article was included in Synthesis in 2010.Recommanded Product: 59669-59-9 This article mentions the following:

Cyclization of 2-[(dimethylamino)methylene]-1,3-bis(dimethylimonio)propane diperchlorate, Me₂NCH:C(CH:N⁺Me₂)₂.2ClO₄^–, with various amino heterocycles led to the formation of a series of fused heterocyclic systems containing a 3-formylpyridine or 5-formylpyrimidine unit. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Recommanded Product: 59669-59-9).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Recommanded Product: 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Identification of pyrazine-based TrkA inhibitors: design, synthesis, evaluation, and computational modeling studies was written by Frett, Brendan;McConnell, Nick;Wang, Yuanxiang;Xu, Zhigang;Ambrose, Andrew;Li, Hong-yu. And the article was included in MedChemComm in 2014.Product Details of 59669-59-9 This article mentions the following:

Trk receptors play a key role in the development and maintenance of neuronal networks. Recent evidence suggests that the Trk family, specifically TrkA, is an important driver for tumor growth, inflammatory and neuropathic pain, and chemoresistance. Through a computational screen, a novel Trk active pharmacophore was identified and a series of pyrazine-based inhibitors were developed, which potently inhibited TrkA. Inhibitors displayed the highest activity on TrkA when screened against a small, tyrosine kinase panel and also exhibited a non-linear SAR. Predicted binding modes of the inhibitors were examined, which identified exploitable regions for future development of more advanced inhibitors. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Product Details of 59669-59-9).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles present in various natural products and synthetic compounds of biological importance like antibacterial, antagonists, antiinflammatory, analgesics, and also show the applications in functional materials. The electrophilic cyclization of various 2-alkynone O-methyl oximes with a wide range of substrates such as ICl, I2, Br2, PhSeBr, etc. provides a variety of 3,4,5-trisubstituted isoxazoles in good to excellent yields.Product Details of 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Identification of 1-(3-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl)-3-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)urea Hydrochloride (CEP-32496), a Highly Potent and Orally Efficacious Inhibitor of V-RAF Murine Sarcoma Viral Oncogene Homologue B1 (BRAF) V600E was written by Rowbottom, Martin W.;Faraoni, Raffaella;Chao, Qi;Campbell, Brian T.;Lai, Andiliy G.;Setti, Eduardo;Ezawa, Maiko;Sprankle, Kelly G.;Abraham, Sunny;Tran, Lan;Struss, Brian;Gibney, Michael;Armstrong, Robert C.;Gunawardane, Ruwanthi N.;Nepomuceno, Ronald R.;Valenta, Ianina;Hua, Helen;Gardner, Michael F.;Cramer, Merryl D.;Gitnick, Dana;Insko, Darren E.;Apuy, Julius L.;Jones-Bolin, Susan;Ghose, Arup K.;Herbertz, Torsten;Ator, Mark A.;Dorsey, Bruce D.;Ruggeri, Bruce;Williams, Michael;Bhagwat, Shripad;James, Joyce;Holladay, Mark W.. And the article was included in Journal of Medicinal Chemistry in 2012.Name: 3-(tert-Butyl)isoxazol-5-amine This article mentions the following:

The Ras/RAF/MEK/ERK mitogen-activated protein kinase (MAPK) signaling pathway plays a central role in the regulation of cell growth, differentiation, and survival. Expression of mutant BRAF^V600E results in constitutive activation of the MAPK pathway, which can lead to uncontrolled cellular growth. Herein, we describe an SAR optimization campaign around a series of quinazoline derived BRAF^V600E inhibitors. In particular, the bioisosteric replacement of a metabolically sensitive tert-Bu group with fluorinated alkyl moieties is described. This effort led directly to the identification of a clin. candidate 1-(3-(6,7-dimethoxyquinazolin-4-yloxy)phenyl)-3-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)urea hydrochloride (CEP-32496, I). CEP-32496 exhibits high potency against several BRAF^V600E-dependent cell lines and selective cytotoxicity for tumor cell lines expressing mutant BRAF^V600E vs. those containing wild-type BRAF. It also exhibits an excellent PK profile across multiple preclin. species. In addition, significant oral efficacy was observed in a 14-day BRAF^V600E-dependent human Colo-205 tumor xenograft mouse model, upon dosing at 30 and 100 mg/kg BID. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Name: 3-(tert-Butyl)isoxazol-5-amine).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. Fe(CO)5 efficiently cleaves the N–O bond of fused isoxazolo-1,4-quinones to give the corresponding imines.All the common reducing reagents failed to open the isoxazole ring.Name: 3-(tert-Butyl)isoxazol-5-amine

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Discovery and optimization of a highly efficacious class of 5-aryl-2-aminopyridines as FMS-like tyrosine kinase 3 (FLT3) inhibitors was written by Liu, Gang;Abraham, Sunny;Liu, Xing;Xu, Shimin;Rooks, Allison M.;Nepomuceno, Ron;Dao, Alan;Brigham, Daniel;Gitnick, Dana;Insko, Darren E.;Gardner, Michael F.;Zarrinkar, Patrick P.;Christopher, Ron;Belli, Barbara;Armstrong, Robert C.;Holladay, Mark W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.SDS of cas: 59669-59-9 This article mentions the following:

Based on a putative binding mode of quizartinib, a potent FMS-like tyrosine kinase 3 (FLT3) inhibitor in Phase III clin. development, the authors have designed de novo a simpler aminopyridine-based hinge binding motif. Further optimization focusing on maximizing in vivo efficacy and minimizing CYP3A4 time-dependent inhibition resulted in a highly efficacious compound I in tumor xenograft model for further preclin. development. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9SDS of cas: 59669-59-9).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. The most common methods for N–O bond cleavage in isoxazoles are hydrogenation with palladium or platinum catalysts or with Raney Ni. Recent developments have shown that Mo(CO)6 efficiently cleaves the N–O bond in isoxazoles.SDS of cas: 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Practical synthesis of 3-amino-5-tert-butylisoxazole from 4,4-dimethyl-3-oxopentanenitrile with hydroxylamine was written by Takase, Akira;Murabayashi, Akira;Sumimoto, Shinzaburo;Ueda, Shiro;Makisumi, Yasuo. And the article was included in Heterocycles in 1991.Computed Properties of C7H12N2O This article mentions the following:

A good yield of 3-amino-5-tert-butylisoxazole (I; R = CMe₃) was obtained regioselectively from a reaction of 4,4-dimethyl-3-oxopentanenitrile with hydroxylamine in aqueous solution adjusted to weakly basic, followed by treatment of the resulting 4,4-dimethyl-3-oxopentaneamidoxime with hydrochloride acid. I (R = Me₂CH, Ph) were prepared in poor yields (27-38%) by the same procedure starting from 4-methyl-3-oxopentanenitrile and benzoylacetonitrile, resp. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Computed Properties of C7H12N2O).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. Isoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.Computed Properties of C7H12N2O

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Synthesis and biological evaluation of new series of quinazoline derivatives as EGFR/HER2 dual-target inhibitors was written by Jiao, Xiaoyu;Zhang, Qing;Zhang, Yue;Shao, Junlan;Ding, Lei;Tang, Chunlei;Feng, Bainian. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2022.Synthetic Route of C7H12N2O This article mentions the following:

It is generally believed that EGFR/HER2 dual-target inhibitors may overcome the resistance of EGFR TKIs caused by HER2 overexpression. The structure-based synthesis and biol. evaluation of quinazoline derivatives as EGFR/HER2 dual-target inhibitors has been studied in this paper. I, II, III, IV displayed comparable inhibitory potency against EGFR and HER2 and I showed remarkable antiproliferative activities against NCI-H358/PC-9/Calu-3/NCI-H1781 (EGFR IC₅₀ = 0.30 nM, HER2 IC₅₀ = 6.07 nM, NCI-H358 GI₅₀ = 23.30 nM, PC-9 GI₅₀ = 1.95 nM, Calu-3 GI₅₀ = 23.13 nM NCI-H1781 GI₅₀ = 41.61 nM). In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Synthetic Route of C7H12N2O).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. The weakness of this bond allows the ring opening of these heterocycles under reductive conditions. Isoxazole can be synthesised via a variety of methods. Examples include via the reaction of hydroxylamine with 1,3-diketones or derivatives of propiolic acid.Synthetic Route of C7H12N2O

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Radical difluoromethylthiolation of aromatics enabled by visible light was written by Li, Jianbin;Zhu, Dianhu;Lv, Leiyang;Li, Chao-Jun. And the article was included in Chemical Science in 2018.Product Details of 59669-59-9 This article mentions the following:

An efficient route to access a valuable catalog of difluoromethyl thioethers RSCHF₂ [R = 1-Me-2-pyrrolyl, 3-indolyl, 2,4,6-(MeO)₃C₆H₂, etc.] via visible-light mediated direct introduction of a difluoromethylthio group (-SCF₂H) to arenes RH under metal-free and mild conditions was reported. This light-mediated protocol successfully converted a broad spectrum of arenes and heteroarenes to difluoromethyl thioethers in the absence of noble metals and stoichiometric amounts of additives. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Product Details of 59669-59-9).

3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9) belongs to isoxazole derivatives. An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. Isoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.Product Details of 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem