Category: 18621-18-6

In 1987,Anthoni, Uffe; Nielsen, Per H.; Smith-Hansen, Lene; Wium-Andersen, Soeren; Christophersen, Carsten published 《Charamin, a quaternary ammonium ion antibiotic from the green alga Chara globularis》.Journal of Organic Chemistry published the findings.Application of 18621-18-6 The information in the text is summarized as follows:

The aqueous extract of the green characean alga C. globularis has antibiotic activity against a natural population of bacteria from pond water. The active component, charamin (I), 4-azoniaspiro[3,3]heptan-2,6-diol, was identified by 1H, 13C NMR, and IR spectroscopy. I was synthesized from azetidin-3-ol by reaction with epichlorohyrin. In the experiment, the researchers used Azetidin-3-ol hydrochloride(cas: 18621-18-6Application of 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.Application of 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

In 2011,Qian, Yimin; Wertheimer, Stanley J.; Ahmad, Mushtaq; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Hamilton, Matthew M.; Hayden, Stuart; Li, Shiming; Marcopulos, Nicholas; McDermott, Lee; Tan, Jenny; Yun, Weiya; Guo, Liang; Pamidimukkala, Anjula; Chen, Yingsi; Huang, Kuo-Sen; Ramsey, Gwendolyn B.; Whittard, Toni; Conde-Knape, Karin; Taub, Rebecca; Rondinone, Cristina M.; Tilley, Jefferson; Bolin, David published 《Discovery of Orally Active Carboxylic Acid Derivatives of 2-Phenyl-5-trifluoromethyloxazole-4-carboxamide as Potent Diacylglycerol Acyltransferase-1 Inhibitors for the Potential Treatment of Obesity and Diabetes》.Journal of Medicinal Chemistry published the findings.Product Details of 18621-18-6 The information in the text is summarized as follows:

Diacylglycerol acyltransferase-1 (DGAT-1) is the enzyme that catalyzes the final and committed step of triglyceride formation, namely, the acylation of diacylglycerol with acyl CoA. DGAT-1 deficient mice demonstrate resistance to weight gain on high fat diet, improved insulin sensitivity, and reduced liver triglyceride content. Inhibition of DGAT-1 thus represents a potential novel approach for the treatment of obesity, dyslipidemia, and metabolic syndrome. In this communication, we report the identification of the lead structure 6 and our lead optimization efforts culminating in the discovery of potent, selective, and orally efficacious carboxylic acid derivatives of 2-phenyl-5-trifluoromethyloxazole-4-carboxamides. In particular, compound 29 (I) (DGAT-1 enzyme assay, IC50 = 57 nM; CHO-K1 cell triglyceride formation assay, EC50 = 0.5 μM) demonstrated dose dependent inhibition of weight gain in diet induced obese (DIO) rats (0.3, 1, and 3 mg/kg, PO, qd) during a 21-day efficacy study. Furthermore, compound 29 demonstrated improved glucose tolerance determined by an oral glucose tolerance test (OGTT). In the experimental materials used by the author, we found Azetidin-3-ol hydrochloride(cas: 18621-18-6Product Details of 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.Product Details of 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

In 2018,Mizojiri, Ryo; Asano, Moriteru; Tomita, Daisuke; Banno, Hiroshi; Nii, Noriyuki; Sasaki, Masako; Sumi, Hiroyuki; Satoh, Yoshihiko; Yamamoto, Yukiko; Moriya, Takeo; Satomi, Yoshinori; Maezaki, Hironobu published 《Discovery of Novel Selective Acetyl-CoA Carboxylase (ACC) 1 Inhibitors》.Journal of Medicinal Chemistry published the findings.Product Details of 18621-18-6 The information in the text is summarized as follows:

The authors initiated structure-activity relationship (SAR) studies for selective ACC1 inhibitors from 1a (N-(1-(2-(3-(3-methylphenoxy)azetidin-1-yl)-1,3-benzoxazol-6-yl)ethyl)acetamide) as a lead compound SAR studies of bicyclic scaffolds revealed many potent and selective ACC1 inhibitors represented by 1f (N-(1-(2-(4-(3-(Cyclopropylmethoxy)phenoxy)phenyl)-1,3-benzoxazol-6-yl)ethyl)acetamide), however most of them had physicochem. issues, particularly low aqueous solubility and potent CYP inhibition. To address these two issues and improve the drug-likeness of this chem. series, the authors converted the bicyclic scaffold into a monocyclic framework. Ultimately, this lead the authors to discover a novel monocyclic derivative 1q (1-((2S)-1-((2-(4-(3-(Cyclopropylmethoxy)phenoxy)phenyl)-1,3-oxazol-5-yl)oxy)propan-2-yl)urea) as a selective ACC1 inhibitor, which showed highly potent and selective ACC1 inhibition as well as acceptable solubility and CYP inhibition profiles. Since compound 1q displayed favorable bioavailability in mouse cassette dosing testing, the authors conducted in vivo PD studies of this compound Oral administration of 1q significantly reduced the concentration of malonyl-CoA in HCT-116 xenograft tumors at doses of more than 30 mg/kg. Accordingly, the authors’ novel series of selective ACC1 inhibitors represents a set of useful orally-available research tools, as well as potential therapeutic agents for cancer and fatty acid related diseases. In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Product Details of 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.Product Details of 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

Kubo, Osamu; Takami, Kazuaki; Kamaura, Masahiro; Watanabe, Koji; Miyashita, Hirohisa; Abe, Shinichi; Matsuda, Kae; Tsujihata, Yoshiyuki; Odani, Tomoyuki; Iwasaki, Shinji; Kitazaki, Tomoyuki; Murata, Toshiki; Sato, Kenjiro published an article in 2021. The article was titled 《Discovery of a novel series of GPR119 agonists: Design, synthesis, and biological evaluation of N-(Piperidin-4-yl)-N-(trifluoromethyl)pyrimidin-4-amine derivatives》, and you may find the article in Bioorganic & Medicinal Chemistry.HPLC of Formula: 18621-18-6 The information in the text is summarized as follows:

The designs, syntheses, and biol. activities of a novel series of N-(piperidin-4-yl)-N-(trifluoromethyl)pyrimidin-4-amine derivatives I [R = Cl, 5-methylsulfonylindolin-1-yl, 4-methylsulfonylcyclohexoxy, etc.; R1 = cyano, tert-butoxycarbonyl, 3-(1-fluoro-1-methyl-ethyl)-1,2,4-oxadiazol-5-yl, etc.] and II [R2 = Cl, (1-tert-butoxycarbonyl-4-piperidyl)amino, (1-tert-butoxycarbonyl-4-piperidyl)-ethyl-amino, etc.] as GPR119 agonists, and to determine the distinctive effect of the N-trifluoromethyl group on hERG inhibition, and also discussed the conformational preference of representative compounds To occupy a presumed hydrophobic space between the pyrimidine and piperidine rings in interaction with GPR119, were replaced the linker oxygen with nitrogen. Subsequently, the introduction of a substituent at the bridging nitrogen atom was explored. We found that the installation of N-trifluoromethyl group I [R = 5-methylsulfonylindolin-1-yl, R1 = tert-butoxycarbonyl] not only enhanced GPR119 agonist activity but also considerably improved the human ether-a-go-go-related gene (hERG) inhibition profile. These improvements were not observed for non-fluorinated substituents, such as Et analog II [R2 = (1-tert-butoxycarbonyl-4-piperidyl)-ethyl-amino]. The next optimization effort focused on the exploration of a new surrogate structure for the indoline ring and the isosteric replacements of the piperidine N-Boc group to improve solubility, metabolic stability, and oral bioavailability. As a result, I [R = 5-methylsulfonylindolin-1-yl, R1 = 3-(1-fluoro-1-methyl-ethyl)-1,2,4-oxadiazol-5-yl] was identified as a potent and orally bioavailable GPR119 agonist. This compound augmented insulin secretion and effectively lowered plasma glucose excursion in a diabetic animal model after oral administration.Azetidin-3-ol hydrochloride(cas: 18621-18-6HPLC of Formula: 18621-18-6) 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.HPLC of Formula: 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

Reference of Azetidin-3-ol hydrochlorideIn 2014 ,《Discovery of Imigliptin, a Novel Selective DPP-4 Inhibitor for the Treatment of Type 2 Diabetes》 was published in ACS Medicinal Chemistry Letters. The article was written by Shu, Chutian; Ge, Hu; Song, Michael; Chen, Jyun-hong; Zhou, Huimin; Qi, Qu; Wang, Feng; Ma, Xifeng; Yang, Xiaolei; Zhang, Genyan; Ding, Yanwei; Zhou, Dapeng; Peng, Peng; Shih, Cheng-kon; Xu, Jun; Wu, Frank. The article contains the following contents:

We report our discovery of a novel series of potent and selective dipeptidyl peptidase IV (DPP-4) inhibitors. Starting from a lead identified by scaffold-hopping approach, our discovery and development efforts were focused on exploring structure-activity relationships, optimizing pharmacokinetic profile, improving in vitro and in vivo efficacy, and evaluating safety profile. The selected candidate, Imigliptin, is now undergoing clin. trial. In the experiment, the researchers used Azetidin-3-ol hydrochloride(cas: 18621-18-6Reference 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.Reference 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 2008,Gobbini, Mauro; Armaroli, Silvia; Banfi, Leonardo; Benicchio, Alessandra; Carzana, Giulio; Fedrizzi, Giorgio; Ferrari, Patrizia; Giacalone, Giuseppe; Giubileo, Michele; Marazzi, Giuseppe; Micheletti, Rosella; Moro, Barbara; Pozzi, Marco; Scotti, Piero Enrico; Torri, Marco; Cerri, Alberto published 《Novel Analogues of Istaroxime, a Potent Inhibitor of Na+,K+-ATPase: Synthesis and Structure-Activity Relationship》.Journal of Medicinal Chemistry published the findings.Product Details of 18621-18-6 The information in the text is summarized as follows:

The authors report the synthesis and biol. properties of novel inhibitors of the Na+,K+-ATPase as pos. inotropic compounds Following the previously described model from which istaroxime was generated, the 5α,14α-androstane skeleton was used as a scaffold to study the space around the basic chain of the lead compound Some compounds demonstrated higher potencies than istaroxime on the receptor and the derivative (I) was the most potent; as further confirmation of the model, the E isomers of the oxime are more potent than the Z form. The compounds tested in the guinea pig model induced pos. inotropic effects, which are correlated to the in vitro inhibitory potency on the Na+,K+-ATPase. The finding that all tested compounds resulted less proarrhythmogenic than digoxin, a currently clin. used pos. inotropic agent, suggests that this could be a feature of the 3-aminoalkyloxime derivative class of 5α,14α-androstane. In the part of experimental materials, we found many familiar compounds, such as Azetidin-3-ol hydrochloride(cas: 18621-18-6Product Details of 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.Product Details of 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

In 2017,Ye, Xiang-Yang; Chen, Stephanie Y.; Wu, Shung; Yoon, David S.; Wang, Haixia; Hong, Zhenqiu; O’Connor, Stephen P.; Li, Jun; Li, James J.; Kennedy, Lawrence J.; Walker, Steven J.; Nayeem, Akbar; Sheriff, Steven; Camac, Daniel M.; Ramamurthy, Vidyhashankar; Morin, Paul E.; Zebo, Rachel; Taylor, Joseph R.; Morgan, Nathan N.; Ponticiello, Randolph P.; Harrity, Thomas; Apedo, Atsu; Golla, Rajasree; Seethala, Ramakrishna; Wang, Mengmeng; Harper, Timothy W.; Sleczka, Bogdan G.; He, Bin; Kirby, Mark; Leahy, David K.; Li, Jianqing; Hanson, Ronald L.; Guo, Zhiwei; Li, Yi-Xin; DiMarco, John D.; Scaringe, Raymond; Maxwell, Brad; Moulin, Frederick; Barrish, Joel C.; Gordon, David A.; Robl, Jeffrey A. published 《Discovery of Clinical Candidate 2-((2S,6S)-2-Phenyl-6-hydroxyadamantan-2-yl)-1-(3′-hydroxyazetidin-1-yl)ethanone [BMS-816336], an Orally Active Novel Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor》.Journal of Medicinal Chemistry published the findings.Formula: C3H8ClNO The information in the text is summarized as follows:

BMS-816336 (6n-2), a hydroxy-substituted adamantyl acetamide, has been identified as a novel, potent inhibitor against human 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) enzyme (IC50 3.0 nM) with >10000-fold selectivity over human 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2). 6n-2 exhibits a robust acute pharmacodynamic effect in cynomolgus monkeys (ED50 0.12 mg/kg) and in DIO mice. It is orally bioavailable (%F ranges from 20 to 72% in preclin. species) and has a predicted pharmacokinetic profile of a high peak to trough ratio and short half-life in humans. This ADME profile met our selection criteria for once daily administration, targeting robust inhibition of 11β-HSD1 enzyme for the first 12 h period after dosing followed by an “”inhibition holiday”” so that the potential for hypothalamic-pituitary-adrenal (HPA) axis activation might be mitigated. 6n-2 was found to be well-tolerated in phase 1 clin. studies and represents a potential new treatment for type 2 diabetes, metabolic syndrome, and other human diseases modulated by glucocorticoid control. 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:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2018,Joncour, Agnes; Desroy, Nicolas; Housseman, Christopher; Bock, Xavier; Bienvenu, Natacha; Cherel, Laetitia; Labeguere, Virginie; Peixoto, Christophe; Annoot, Denis; Lepissier, Luce; Heiermann, Jorg; Hengeveld, Willem Jan; Pilzak, Gregor; Monjardet, Alain; Wakselman, Emanuelle; Roncoroni, Veronique; Le Tallec, Sandrine; Galien, Rene; David, Christelle; Vandervoort, Nele; Christophe, Thierry; Conrath, Katja; Jans, Mia; Wohlkonig, Alexandre; Soror, Sameh; Steyaert, Jan; Touitou, Robert; Fleury, Damien; Vercheval, Lionel; Mollat, Patrick; Triballeau, Nicolas; van der Aar, Ellen; Brys, Reginald; Heckmann, Bertrand published 《Correction to Discovery, Structure-Activity Relationship, and Binding Mode of an Imidazo[1,2-a]pyridine Series of Autotaxin Inhibitors [Erratum to document cited in CA167:306993]》.Journal of Medicinal Chemistry published the findings.Related Products of 18621-18-6 The information in the text is summarized as follows:

In the original publication, Page 7371, In line 5 of the author listing, author Sameh Soror should have a second affiliation: “”Center of Scientific Excellence, Helwan Structural Biol. Research, Faculty ofPharmacy, Helwan University, Cairo, Egypt””; the correction is provided here. In addition to this study using Azetidin-3-ol hydrochloride, there are many other studies that have used Azetidin-3-ol hydrochloride(cas: 18621-18-6Related Products of 18621-18-6) 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.Related Products of 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

In 1996,Dave, Paritosh R. published 《Acylative Dealkylation of N-tert-Butyl-3-substituted Azetidines: Facile Access to [1.1.0]Azabicyclobutane, 3-Hydroxyazetidinium Hydrochloride, and 3-Azetidinones》.Journal of Organic Chemistry published the findings.Safety of Azetidin-3-ol hydrochloride The information in the text is summarized as follows:

A novel acylative dealkylation of N-tert-butylazetidines and its application to the facile high-yield syntheses of [1.1.0]azabicyclobutane, 3-hydroxyazetidinium hydrochloride, and 3-azetidinones is described. In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Safety 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.Safety 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

《α-Lithiation-Electrophile Trapping of N-Thiopivaloylazetidin-3-ol: Stereoselective Synthesis of 2-Substituted 3-Hydroxyazetidines》 was written by Hodgson, David M.; Pearson, Christopher I.; Thompson, Amber L.. Name: Azetidin-3-ol hydrochlorideThis research focused onthiopivaloylazetidinol alpha lithiation electrophile trapping; hydroxyazetidine substituted derivative stereoselective preparation deuterium labeling. The article conveys some information:

α-Lithiation of N-thiopivaloylazetidin-3-ol and subsequent electrophile trapping provides access to a range of 2-substituted 3-hydroxyazetidines with generally good trans-diastereoselectivity, aside from deuteration, which gives the cis-diastereoisomer. Deuterium labeling studies indicate that the initial α-deprotonation occurs preferentially, but not exclusively, in a trans-selective manner. These studies also suggest that the stereochem. outcome of the electrophile trapping depends on the electrophile used but is independent of which α-proton (cis or trans to the hydroxyl group) is initially removed. The results came from multiple reactions, including the reaction of Azetidin-3-ol hydrochloride(cas: 18621-18-6Name: 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.Name: 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