Heterocyclic Building Blocks-isoxazole

2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 3: Synthesis and activity of isosteric analogs was written by Kai, Hiroyuki;Morioka, Yasuhide;Koriyama, Yuji;Okamoto, Kazuya;Hasegawa, Yasushi;Hattori, Maki;Koike, Katsumi;Chiba, Hiroki;Shinohara, Shunji;Iwamoto, Yuka;Takahashi, Kohji;Tanimoto, Norihiko. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Application of 59669-59-9 This article mentions the following:

Structure-activity relationships and efforts to optimize the pharmacokinetic profile of isosteric analogs of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among those examined, compound I showed potent affinity for cannabinoid receptor 1 (CB1) and receptor 2 (CB2). This compound displayed oral bioavailability and analgesic activity. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Application of 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. 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.Application of 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

AgNTf₂-catalyzed formal [3+2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives was written by Cao, Ziping;Zhu, Jiekun;Liu, Li;Pang, Yuanling;Tian, Laijin;Sun, Xuejun;Meng, Xin. And the article was included in Beilstein Journal of Organic Chemistry in 2019.Formula: C7H12N2O This article mentions the following:

A formal [3 + 2] cycloaddition between ynamides RCCN(R¹C₆H₅)R² (R = H, 2-Me, 4-F, 3-Me, etc.; R¹ = Me, Bn, Ph, etc.; R² = Ts, Ms, o-Ns, p-Ns) and unprotected isoxazol-5-amines I (R³ = Me, Ph, i-Pr, etc.) has been developed in the presence of catalytic AgNTf₂ in an open flask. By the protocol, a variety of functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives II can be obtained in up to 99% yield. The reaction mechanism might involve the generation of an unusual alpha-imino silver carbene intermediate (or a silver-stabilized carbocation) and subsequent cyclization/isomerization to build the significant pyrrole-3-carboxamide motif. The reaction features the use of an inexpensive catalyst, simple reaction conditions, simple work-up without column chromatog. purification for most of products and high yields. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Formula: C7H12N2O).

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. 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.Formula: C7H12N2O

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Discovery of a new class of p38 kinase inhibitors was written by Dumas, J.;Sibley, R.;Riedl, B.;Monahan, M. K.;Lee, W.;Lowinger, T. B.;Redman, A. M.;Johnson, J. S.;Kingery-Wood, J.;Scott, W. J.;Smith, R. A.;Bobko, M.;Schoenleber, R.;Ranges, G. E.;Housley, T. J.;Bhargava, A.;Wilhelm, S. M.;Shrikhande, A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2000.Category: isoxazole This article mentions the following:

The MAP kinase p38 has been implicated in cytokine signaling, and its inhibitors are potentially useful for the treatment of arthritis and osteoporosis. Novel small-mol. inhibitors of p38 kinase were derived from a combinatorial chem. effort and exhibit activity in the nanomolar range. Very steep structure-activity relationships are observed within this class. 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. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. 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.Category: isoxazole

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion was written by Ge, Yun;Sun, Wangbin;Chen, Yang;Huang, Yulin;Liu, Zhuang;Jiang, Yaojia;Loh, Teck-Peng. And the article was included in Journal of Organic Chemistry in 2019.Recommanded Product: 59669-59-9 This article mentions the following:

A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the Wolff rearrangement reactions, the N-isoxazole amides are accessed as the sole products under thermal conditions. On the other hand, α-amino acid derivatives of N-isoxazoles can be obtained through N-H insertion reactions in the presence of catalytic Rh₂(Oct)₄. Both reactions proceed under mild reaction conditions and feature a broad substrate scope. 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.Synthetically, isoxazoles serve as valuable precursors for the construction of diverse molecules, including many natural products. Some alternative routes for the synthesis of isoxazoles have also been developed and reported. The 2-benzoyl-2-halo-2H-azirines provide 4-haloisoxazoles in good yields after heating in toluene at reflux temperature.Recommanded Product: 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Synthesis and biological evaluation of diaryl urea derivatives as FLT3 inhibitors was written by Zhang, Qing;Zhao, Kuantao;Zhang, Lixun;Jiao, Xiaoyu;Zhang, Yongjie;Tang, Chunlei. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.Quality Control of 3-(tert-Butyl)isoxazol-5-amine This article mentions the following:

As a class III receptor tyrosine kinase (RTK), FMS-like tyrosine kinase 3 (FLT3) is always overexpressed in many cases of acute leukemia. This paper studies the structure-based synthesis and biol. evaluation of diaryl urea derivatives as FLT3 inhibitors. Encouragingly, compounds 1-(3-(tert-butyl)isoxazol-5-yl)-3-(4-(7-methoxybenzo[d]imidazo[2,1-b]thiazol-2-yl)phenyl)urea , 1-(3-(tert-butyl)isoxazol-5-yl)-3-(4-(7-(2-morpholinoethoxy)benzo[d]imidazo[2,1-b]thiazol-2-yl)phenyl)urea , 1-(5-(tert-butyl)isoxazol-3-yl)-3-(2-(4-(2-morpholinoethoxy)phenyl)benzo[d]imidazo[2,1-b]thiazol-7-yl)urea , and 1-(3-(tert-butyl)isoxazol-5-yl)-3-(2-(4-(2-morpholinoethoxy)phenyl)benzo[d]imidazo[2,1-b]thiazol-7-yl)urea showed excellent biol. activities in a low nanomolar range. In particular, compound 1-(3-(tert-butyl)isoxazol-5-yl)-3-(4-(7-(2-morpholinoethoxy)benzo[d]imidazo[2,1-b]thiazol-2-yl)phenyl)urea demonstrated significant inhibitory potency against FLT3-ITD (IC₅₀ = 5.60 nM) and better antiproliferative activity than quizartinib against MV4-11 cell line (IC₅₀ = 0.176 nM). Compound 1-(3-(tert-butyl)isoxazol-5-yl)-3-(4-(7-(2-morpholinoethoxy)benzo[d]imidazo[2,1-b]thiazol-2-yl)phenyl)urea for the treatment of acute myeloid leukemia could be very promising. 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. Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter. Some alternative routes for the synthesis of isoxazoles have also been developed and reported. The 2-benzoyl-2-halo-2H-azirines provide 4-haloisoxazoles in good yields after heating in toluene at reflux temperature.Quality Control of 3-(tert-Butyl)isoxazol-5-amine

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

C-H chlorination of (hetero)anilines via photo/organo co-catalysis was written by Xie, Wuchen;Wang, Meng;Yang, Siyu;Chen, Yadong;Feng, Jie;Huang, Yatian. And the article was included in Organic & Biomolecular Chemistry in 2022.Name: 3-(tert-Butyl)isoxazol-5-amine This article mentions the following:

Herein, a photo-redox and organo co-catalyzed chlorination method for anilines to gave chloro-anilines ArNR¹R² [Ar = 4-ClC₆H₄, 3,4-di-Cl-5-FC₆H₂, 4-Cl-2,5-di-FC₆H₂, etc.; R¹ = H, Me; R² = H, Me, C(O)Me, Ph, pyrimidin-2-yl; R¹R² = (CH₂)₂N(CH₃)(CH₂)₂] was disclose. This method had great substrate generality and excellent mono-chlorination selectivity. Another merit of this method was the late-stage modification of drug mols., which would be useful in medicinal chem. 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. 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.Name: 3-(tert-Butyl)isoxazol-5-amine

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model was written by Li, Guo-Bo;Ma, Shuang;Yang, Ling-Ling;Ji, Sen;Fang, Zhen;Zhang, Guo;Wang, Li-Jiao;Zhong, Jie-Min;Xiong, Yu;Wang, Jiang-Hong;Huang, Shen-Zhen;Li, Lin-Li;Xiang, Rong;Niu, Dawen;Chen, Ying-Chun;Yang, Sheng-Yong. And the article was included in Journal of Medicinal Chemistry in 2016.Category: isoxazole This article mentions the following:

Psoriasis is a chronic T-cell-mediated autoimmune disease, and FMS-like tyrosine kinase 3 (FLT3) has been considered as a potential mol. target for the treatment of psoriasis. In this investigation, structural optimization was performed on a lead compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3- (trifluoromethyl)phenyl)urea, which showed a moderate inhibitory activity against FLT3. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship anal. led to the discovery of a number of potent FLT3 inhibitors. One of the most active compounds, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (I), was then chosen for in-depth anti-psoriasis studies because this compound displayed the highest potency in a preliminary anti-psoriasis test. Compound I exhibited significant anti-psoriatic effects in the K14-VEGF transgenic mouse model of psoriasis, and no recurrence was found 15 days later after the last administration. Detailed mechanisms of action of compound I were also investigated. Collectively, compound I could be a potential drug candidate for psoriasis treatment. 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. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. 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.Category: isoxazole

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Design and Synthesis of New Thiophene/Thieno[2,3-d]pyrimidines along with Their Cytotoxic Biological Evaluation as Tyrosine Kinase Inhibitors in Addition to Their Apoptotic and Autophagic Induction was written by Elmongy, Elshaymaa I.;Attallah, Nashwah G. M.;Altwaijry, Najla;AlKahtani, Manal Mubarak;Henidi, Hanan Ali. And the article was included in Molecules in 2022.Synthetic Route of C7H12N2O This article mentions the following:

This work describes the synthesis and anticancer activity against kinase enzymes of newly designed thiophene and thieno[2,3-d]pyrimidines I [R = 2-(2-chloroacetyl)hydrazino, (3-methyl-2,5-dioxo-pyrrol-1-yl)amino, 2-[2-[(5-tert-butylisoxazol-3-yl)amino]acetyl]hydrazino, etc.] and II [R¹ = Cl, (5-tert-butylisoxazol-3-yl)amino, (3-tert-butylisoxazol-5-yl)amino] along with their potential to activate autophagic and apoptotic cell death in cancer cells. The designed compounds were scanned for their affinity for kinases. The results were promising with affinity ranges from 46.7% to 13.3%. Mol. docking studies were performed, and the compounds were then screened for their antiproliferative effects. Interestingly, compounds I [R = 2-(2-chloroacetyl)hydrazino, (3-methyl-2,5-dioxo-pyrrol-1-yl)amino] resulted in higher cytotoxic effects than the reference standard against MCF-7 and HepG-2. The compounds were evaluated for their induction of apoptosis and/or necrosis on HT-29 and HepG-2. Three compounds induced significant early apoptosis compared to untreated control HT-29 cells, and four derivatives were more significant compared to untreated HepG-2 cells. Further investigated the effect of four compounds on the autophagy process within HT-29, HepG-2, and MCF-7 cells with flow cytometry. Similar to the apoptosis results, I [R = 2-(2-chloroacetyl)hydrazino] showed the highest autophagic induction among all compounds The potential inhibitory activity of the synthesized compounds on kinases was assessed. Screened compounds showed inhibition activity ranging from 41.4% to 83.5%. Compounds recorded significant inhibition were further investigated for their specific FLT3 kinase inhibitory activity. Noticeably, I [R = 2-(2-chloroacetyl)hydrazino] exhibited the highest inhibitory activity against FLT3. 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 also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. 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.Synthetic Route of C7H12N2O

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Synthesis and biological evaluation of novel 5,6-dihydrobenzo[h]quinazoline derivatives as FLT3 inhibitors was written by Ding, Lei;Zhang, Qing;Zhao, Kuantao;Jiao, Xiaoyu;Zhou, Ying;Fan, Weizheng;Tang, Chunlei. And the article was included in Chemical Biology & Drug Design in 2022.Recommanded Product: 3-(tert-Butyl)isoxazol-5-amine This article mentions the following:

Fms-like tyrosine kinase 3 (FLT3) is widely expressed and often mutated in acute myeloid leukemia (AML), which makes it an important target for the treatment of AML. The structure-based synthesis and biol. evaluation of 5,6-dihydrobenzo[h]quinazoline derivatives as FLT3 inhibitors have been studied in this paper. Compound I derivatives (X and Y = N, CH, CF, or CCH₃ and R = isoxazole derivatives) displayed comparable inhibitory potency against FLT3-ITD and showed remarkable antiproliferative activities against MV4-11. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)isoxazol-5-amine (cas: 59669-59-9Recommanded Product: 3-(tert-Butyl)isoxazol-5-amine).

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. As with isoxazolines, isoxazoles may be cleaved using low-valent titanium obtained from the Kulinkovich reaction.This procedure affords enaminoketones from 2,4-substituted isoxazoles.Recommanded Product: 3-(tert-Butyl)isoxazol-5-amine

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

ClTi(OⁱPr)₃-Promoted Reductive Amination on the Solid Phase: Combinatorial Synthesis of a Biaryl-Based Sulfonamide Library was written by Gutierrez, Corey D.;Bavetsias, Vassilios;McDonald, Edward. And the article was included in Journal of Combinatorial Chemistry in 2008.Product Details of 59669-59-9 This article mentions the following:

A combinatorial library (9 amines × 7 sulfonyl chlorides × 13 boronic acids = 819 compounds) was produced on solid support in a four-step sequence, i.e., ClTi(OⁱPr)₃-promoted reductive amination, sulfonylation of the resin-bound amine, Suzuki cross-coupling, and acid-mediated cleavage. The library members (e.g. I) were obtained in moderate quantity (1-8 mg) with over 70% of the sampled products greater than 90% pure according to LC-MS anal. 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. 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.Product Details of 59669-59-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem