Category: 18621-18-6

In 1974,Okutani, Tetsuya; Kaneko, Tatsuhiko; Masuda, Katsutada published 《Azetidine derivatives. I. Synthesis o f 3-substituted azetidine derivatives》.Chemical & Pharmaceutical Bulletin published the findings.Formula: C3H8ClNO The information in the text is summarized as follows:

The azetidinols I (R = OH; R1 = Me2CH, Me3C, cyclohexyl, PhCHMe; R2 = H) were prepared by treating R1NH2 with epichlorohydrin followed by MeCN. I (R = OH, R1 = Et, R2 = H) was prepared from I (R = OH, R1 = R2 = H) and EtI. cis- and trans-I (R = OH, R1 = cyclohexyl, R2 = Ph) were prepared by bromination of PhCH:CHCH2Cl followed by treatment with cyclohexylamine. I (R = OH; R1 = Me2CH, Me3C, tert-octyl, cyclohexyl, PhCHMe, 1-adamantyl; R2 = H) were converted to I [R = MeSO3, NH2, CN, CO2H, NHC(:NH)NH2]. I [R = NHC(:NH)NH2] were antihypertensives (no data). In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Formula: C3H8ClNO)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Formula: C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
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Alcohols – Chemistry LibreTexts

Computed Properties of C3H8ClNOIn 2018 ,《Phenylthiazoles with tert-Butyl side chain: Metabolically stable with anti-biofilm activity》 was published in European Journal of Medicinal Chemistry. The article was written by Kotb, Ahmed; Abutaleb, Nader S.; Seleem, Mohamed A.; Hagras, Mohamed; Mohammad, Haroon; Bayoumi, Ashraf; Ghiaty, Adel; Seleem, Mohamed N.; Mayhoub, Abdelrahman S.. The article contains the following contents:

(Tert-butylphenyl)thiazolylpyrimidines I [R = H2N, MeNH, 1-pyrrolidinyl, 3-pyridinyl, EtNH, cyclopentylamino, cyclohexylamino, Me2N, 1-azetidinyl, 3-hydroxy-1-azetidinyl, 4-morpholinyl, H2NCH2CH2NH, H2NNH, tetramethylguanidinyl, R1C(:NH)NH; R1 = H2N, MeNH, Me2N, 1-pyrrolidinyl, 4-morpholinyl, 4-methyl-1-piperazinyl, 3-pyridinyl, 2-pyridinyl] were prepared as antibacterial agents and tested against methicillin-resistant Staphylococcus aureus (MRSA). I [R = H2NCH2CH2NH, R1C(:NH)NH; R1 = Me2N, 4-morpholinyl, 3-pyridinyl, 2-pyridinyl] were tested against vancomycin-resistant Staphylococcus aureus, methicillin- and cephalosporin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus epidermidis, Enterococcus faecalis, and Listeria monocytogenes, were tested for toxicity to human colorectal cells, and were tested for activity against MRSA biofilms. I (R = H2NCH2CH2NH) was tested for its stimulation of resistance in MRSA and for its pharmacokinetic properties (half-life, clearance, volumes fo distribution). The results came from multiple reactions, including the reaction of Azetidin-3-ol hydrochloride(cas: 18621-18-6Computed Properties of C3H8ClNO)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Computed Properties of C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

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Alcohol – Wikipedia,
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In 1968,Chatterjee, Shym S.; Triggle, D. J. published 《Synthesis of azetidin-3-ol》.Chemical Communications (London) published the findings.Recommanded Product: 18621-18-6 The information in the text is summarized as follows:

Ph2CHNHCH2CH(OH)CH2Cl, m. 201° (HCl salt), prepared from benzhydrylamine and 1-chloro-2,3-epoxypropane (I), was cyclized to 1-(diphenylmethyl)azetidin-3-ol (II), m. 115°. Hydrogenation of II (as the HCl salt)in EtOH at 60 psi. with 5% Pd-C catalyst gave azetidin-3-ol (III) HCl salt, m. 91-2°. Attempts to prepare III from benzylamine and I failed, since 3-chloro-1-(benzylamino)-2-hydroxypropane could not be cyclized. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6Recommanded Product: 18621-18-6)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Recommanded Product: 18621-18-6 Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《Novel syntheses of 1,3,3-trinitroazetidine》 was written by Katritzky, Alan R.; Cundy, Darren J.; Chen, Jie. Recommanded Product: Azetidin-3-ol hydrochlorideThis research focused ontrinitroazetidine TNAZ. The article conveys some information:

Alternative methods for the synthesis of 1,3,3-trinitroazetidine (TNAZ) from epichlorohydrin and benzhydrylamine have been developed. These approaches employ N-sulfonyl-3-(hydroxyimino)azetidines as penultimate intermediates and represent an improvement over previously published methods which require either diazo containing intermediates or involve low yielding procedures. Parallel methods employing N-benzhydryl- and N-benzyl-3-(hydroxyimino)azetidine were also investigated as alternate routes to TNAZ. In addition to this study using Azetidin-3-ol hydrochloride, there are many other studies that have used Azetidin-3-ol hydrochloride(cas: 18621-18-6Recommanded Product: Azetidin-3-ol hydrochloride) was used in this study.

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Recommanded Product: Azetidin-3-ol hydrochloride Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2016,Kinzel, Olaf; Steeneck, Christoph; Schlueter, Thomas; Schulz, Andreas; Gege, Christian; Hahn, Ulrike; Hambruch, Eva; Hornberger, Martin; Spalwisz, Adriana; Frick, Katharina; Perovic-Ottstadt, Sanja; Deuschle, Ulrich; Burnet, Michael; Kremoser, Claus published 《Novel substituted isoxazole FXR agonists with cyclopropyl, hydroxycyclobutyl and hydroxyazetidinyl linkers: Understanding and improving key determinants of pharmacological properties》.Bioorganic & Medicinal Chemistry Letters published the findings.COA of Formula: C3H8ClNO The information in the text is summarized as follows:

Several isoxazole-containing series of FXR agonists have been published over the last 15 years, subsequent to the prototypical amphiphilic ‘hammerhead’-type structure that was originally laid out by GW4064, the first potent synthetic FXR agonist. A set of novel compounds where the hammerhead is connected to the terminal carboxylic acid-bearing aryl or heteroaryl moiety by either a cyclopropyl, a hydroxycyclobutyl or a hydroxyazetidinyl linker was synthesized in order to improve upon the ADME properties of such isoxazoles. The resulting compounds all demonstrated high potencies at the target receptor FXR but with considerable differences in their physicochem. and in vivo profiles. The structure-activity relationships for key chem. features that have a major impact on the in vivo pharmacol. of this series are discussed. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6COA of Formula: C3H8ClNO)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.COA of Formula: C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2022,Ikeda, Shuhei; Kajita, Yuichi; Miyamoto, Maki; Matsumiya, Kouta; Ishii, Tsuyoshi; Nishi, Toshiya; Gay, Sean C.; Lane, Weston; Constantinescu, Cristian C.; Alagille, David; Papin, Caroline; Tamagnan, Gilles; Kuroita, Takanobu; Koike, Tatsuki published an article in European Journal of Medicinal Chemistry. The title of the article was 《Design and synthesis of aryl-piperidine derivatives as potent and selective PET tracers for cholesterol 24-hydroxylase (CH24H)》.Recommanded Product: 18621-18-6 The author mentioned the following in the article:

Cholesterol 24-hydroxylase (CH24H, CYP46A1) is a cytochrome P 450 family enzyme that maintains the homeostasis of brain cholesterol. Soticlestat, a potent and selective CH24H inhibitor, is in development as a therapeutic agent for Dravet syndrome and Lennox-Gastaut syndrome. Herein, we report the discovery of aryl-piperidine derivatives as potent and selective CH24H positron emission tomog. (PET) tracers which can be used for dose guidance of a clin. CH24H inhibitor and as a diagnostic tool for CH24H-related pathol. Starting from compound I (IC50 = 16 nM, logD = 1.7), which was reported as a CH24H inhibitor with lower lipophilicity, a 18F-labeling site (3-fluoroazetidine) was incorporated by structure-based drug design (SBDD) utilizing the co-crystal structure of a compound I analog. Subsequent optimization to adjust key parameters for PET tracers, such as potency, lipophilicity, brain penetration, and unbound plasma protein binding, enabled compound II [Ar = 4-FC6H4, X = N] (IC50 = 8.8 nM) and compound II [Ar = 4-chloropyrazol-1-yl, X = CH] (IC50 = 8.7 nM) as PET imaging candidates. Selectivity of these compounds for CH24H was validated by a brain distribution study using CH24H-WT and KO mice. In non-human primate PET imaging, [18F] labeled analogs showed similar regional uptake in the brain, indicating that these tracers were specific to the CH24H-expressed regions and validated the expression of CH24H in the living brain by different tracers. After reading the article, we found that the author used Azetidin-3-ol hydrochloride(cas: 18621-18-6Recommanded Product: 18621-18-6)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Recommanded Product: 18621-18-6 Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

COA of Formula: C3H8ClNOIn 2014 ,《Design, Synthesis, and Evaluation of Nonretinoid Retinol Binding Protein 4 Antagonists for the Potential Treatment of Atrophic Age-Related Macular Degeneration and Stargardt Disease》 appeared in Journal of Medicinal Chemistry. The author of the article were Cioffi, Christopher L.; Dobri, Nicoleta; Freeman, Emily E.; Conlon, Michael P.; Chen, Ping; Stafford, Douglas G.; Schwarz, Daniel M. C.; Golden, Kathy C.; Zhu, Lei; Kitchen, Douglas B.; Barnes, Keith D.; Racz, Boglarka; Qin, Qiong; Michelotti, Enrique; Cywin, Charles L.; Martin, William H.; Pearson, Paul G.; Johnson, Graham; Petrukhin, Konstantin. The article conveys some information:

Accumulation of lipofuscin in the retina is associated with pathogenesis of atrophic age-related macular degeneration and Stargardt disease. Lipofuscin bisretinoids (exemplified by N-retinylidene-N-retinylethanolamine) seem to mediate lipofuscin toxicity. Synthesis of lipofuscin bisretinoids depends on the influx of retinol from serum to the retina. Compounds antagonizing the retinol-dependent interaction of retinol-binding protein 4 (RBP4) with transthyretin in the serum would reduce serum RBP4 and retinol and inhibit bisretinoid formation. The authors recently showed that I, a potent carboxylic acid based RBP4 antagonist, can significantly reduce lipofuscin bisretinoid formation in the retinas of Abca4-/- mice. As part of the NIH Blueprint Neurotherapeutics Network project the authors undertook the in vitro exploration to identify novel conformationally flexible and constrained RBP4 antagonists with improved potency and metabolic stability. The authors also demonstrate that upon acute and chronic dosing in rats, II, a potent cyclopentyl fused pyrrolidine antagonist, reduced circulating plasma RBP4 protein levels by approx. 60%. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6COA of Formula: C3H8ClNO)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.COA of Formula: C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2015,Wang, Zhaobin; Sheong, Fu Kit; Sung, Herman H. Y.; Williams, Ian D.; Lin, Zhenyang; Sun, Jianwei published 《Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines》.Journal of the American Chemical Society published the findings.Electric Literature of C3H8ClNO The information in the text is summarized as follows:

The first catalytic asym. desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermol. reactions were realized with excellent efficiency and enantioselectivity. These were enabled by the suitable combination of catalyst, nucleophile, protective group, and reaction conditions. The highly enantioenriched densely functionalized products are versatile precursors to other useful chiral mols. Mechanistic studies, including DFT calculations, revealed that only one catalyst mol. is involved in the key transition state, though both reactants can be activated. Also, the Curtin-Hammett principle dictates the reaction proceeds via amide nitrogen activation. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6Electric Literature of C3H8ClNO)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Electric Literature of C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2013,Ishida, Naoki; Shimamoto, Yasuhiro; Yano, Takaaki; Murakami, Masahiro published 《1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams》.Journal of the American Chemical Society published the findings.Quality Control of Azetidin-3-ol hydrochloride The information in the text is summarized as follows:

In the presence of [Rh(COD)(OH)]2 and the nonracemic bibenzodioxolediphosphine (R)-difluorphos, 1-arylsulfonyl-3-aryl-3-azetidinols such as I (R = Ph, 4-MeOC6H4, 4-F3CC6H4; Ts = 4-MeC6H4SO2) underwent enantioselective rearrangement to give fused thiazinediones such as II (R = Ph, 4-MeOC6H4, 4-F3CC6H4) in 90-95% yields and in 91:9-93:7 er. Stereoselective rearrangement of nonracemic amino acid-derived 1-arylsulfonyl-3-aryl-3-azetidinols such as III (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) in the presence of racemic 2,2′-bis{bis(3,5-xylyl)phosphino}-1,1′-binaphthyl yielded fused dihydrohydroxythiazinediones such as IV (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) as single diastereomers and enantiomers in 97-99% yields. Rearrangement of I (R = Ph) with a perdeuterated tosyl group yielded a deuterated product monolabeled at the N-Me group; a mechanism for the rearrangement is proposed. The structure of IV (R1 = Ph; R2 = Me; R3 = Me; R4 = H) was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Quality Control of Azetidin-3-ol hydrochloride)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Quality Control of Azetidin-3-ol hydrochloride Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2006,Barnes, David M.; Christesen, Alan C.; Engstrom, Kenneth M.; Haight, Anthony R.; Hsu, Margaret C.; Lee, Elaine C.; Peterson, Matthew J.; Plata, Daniel J.; Raje, Prasad S.; Stoner, Eric J.; Tedrow, Jason S.; Wagaw, Seble published 《Chlorination at the 8-Position of a Functionalized Quinolone and the Synthesis of Quinolone Antibiotic ABT-492》.Organic Process Research & Development published the findings.Category: alcohols-buliding-blocks The information in the text is summarized as follows:

The total synthesis of quinolone antibiotic ABT-492 (I) has been achieved in 67% yield over nine steps from 2,4,5-trifluorobenzoic acid. The highlights of this synthesis include a novel chemoselective chlorination at the 8-position of a highly elaborated quinolone core. In addition, a Lewis acid promoted cyclization reaction to form the quinolone heterocycle was developed which was incorporated into a one-pot, three-step cyclization/coupling/protection sequence that proceeds in 93% yield. In addition to this study using Azetidin-3-ol hydrochloride, there are many other studies that have used Azetidin-3-ol hydrochloride(cas: 18621-18-6Category: alcohols-buliding-blocks) was used in this study.

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Category: alcohols-buliding-blocks Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts