Category: 18621-18-6

In 1999,Hayashi, Kazuhiko; Sato, Chisato; Hiki, Shinsuke; Kumagai, Toshio; Tamai, Satoshi; Abe, Takao; Nagao, Yoshimitsu published 《Novel efficient synthesis of 1-azabicyclo[1.1.0]butane and its application to the synthesis of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol useful for the pendant moiety of an oral 1β-methylcarbapenem antibiotic L-084》.Tetrahedron Letters published the findings.Product Details of 18621-18-6 The information in the text is summarized as follows:

1-Azabicyclo[1.1.0]butane was successfully synthesized by treatment of 2,3-dibromopropylamine hydrobromide with organolithium compounds and was readily converted to 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride and versatile 3-hydroxyazetidine hydrochloride and 3-bromoazetidine hydrobromide. 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 2006,Isoda, Takeshi; Ushirogochi, Hideki; Satoh, Koichi; Takasaki, Tsuyoshi; Yamamura, Itsuki; Sato, Chisato; Mihira, Ado; Abe, Takao; Tamai, Satoshi; Yamamoto, Shigeki; Kumagai, Toshio; Nagao, Yoshimitsu published 《Syntheses and pharmacokinetic studies of prodrug esters for the development of oral carbapenem, L-084》.Journal of Antibiotics published the findings.Application of 18621-18-6 The information in the text is summarized as follows:

We discovered an orally active carbapenem, L-084, through pharmacokinetic studies on various prodrug esters of (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio-1-carbapen-2-em-3-carboxylic acid (LJC11,036). L-084 showed a strong antimicrobial activity against Gram-pos. and Gram-neg. bacteria and exhibited the highest intestinal absorption among synthesized prodrugs of LJC11,036. In the experimental materials used by the author, we found 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

Gulati, Anmol; Yeung, Charles S.; Lapointe, Blair; Kattar, Solomon D.; Gunaydin, Hakan; Scott, Jack D.; Childers, Kaleen K.; Methot, Joey L.; Simov, Vladimir; Kurukulasuriya, Ravi; Pio, Barbara; Morriello, Greg J.; Liu, Ping; Tang, Haiqun; Neelamkavil, Santhosh; Wood, Harold B.; Rada, Vanessa L.; Ardolino, Michael J.; Yan, Xin Cindy; Palte, Rachel; Otte, Karin; Faltus, Robert; Woodhouse, Janice; Hegde, Laxminarayan G.; Ciaccio, Paul; Minnihan, Ellen C.; DiMauro, Erin F.; Fell, Matthew J.; Fuller, Peter H.; Ellis, J. Michael published their research in RSC Medicinal Chemistry in 2021. The article was titled 《Optimization of brain-penetrant picolinamide derived leucine-rich repeat kinase 2 (LRRK2) inhibitors》.Computed Properties of C3H8ClNO The article contains the following contents:

The discovery of potent, kinome selective, brain penetrant LRRK2 inhibitors is the focus of extensive research seeking new, disease-modifying treatments for Parkinson′s disease (PD). Herein, we describe the discovery and evolution of a picolinamide-derived lead series. Our initial optimization efforts aimed at improving the potency and CLK2 off-target selectivity of compound 1 by modifying the heteroaryl C-H hinge and linker regions. This resulted in compound 12 which advanced deep into our research operating plan (ROP) before heteroaryl aniline metabolite 14 was characterized as Ames mutagenic, halting its progression. Strategic modifications to our ROP were made to enable early de-risking of putative aniline metabolites or hydrolysis products for mutagenicity in Ames. This led to the discovery of 3,5-diaminopyridine 15 and 4,6-diaminopyrimidine 16 as low risk for mutagenicity (defined by a 3-strain Ames neg. result). Anal. of key matched mol. pairs 17 and 18 led to the prioritization of the 3,5-diaminopyridine sub-series for further optimization due to enhanced rodent brain penetration. These efforts culminated in the discovery of Et trifluoromethyl pyrazole 23 with excellent LRRK2 potency and expanded selectivity vs. off-target CLK2. In the part of experimental materials, we found many familiar compounds, such as 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.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application In Synthesis of Azetidin-3-ol hydrochlorideIn 2017 ,《Design, Synthesis, and Structure-Activity Relationship of Tetrahydropyrido[4,3-d]pyrimidine Derivatives as Potent Smoothened Antagonists with in Vivo Activity》 was published in ACS Chemical Neuroscience. The article was written by Lu, Wenfeng; Liu, Yongqiang; Ma, Haikuo; Zheng, Jiyue; Tian, Sheng; Sun, Zhijian; Luo, Lusong; Li, Jiajun; Zhang, Hongjian; Yang, Zeng-Jie; Zhang, Xiaohu. The article contains the following contents:

Abstract: Medulloblastoma is one of the most prevalent brain tumors in children. Aberrant hedgehog (Hh) pathway signaling is thought to be involved in the initiation and development of medulloblastoma. Vismodegib, the first FDA-approved cancer therapy based on inhibition of aberrant hedgehog signaling, targets smoothened (Smo), a G-protein coupled receptor (GPCR) central to the Hh pathway. Although vismodegib exhibits promising therapeutic efficacy in tumor treatment, concerns have been raised from its nonlinear pharmacokinetic (PK) profiles at high doses partly due to low aqueous solubility Many patients experience adverse events such as muscle spasms and weight loss. In addition, drug resistance often arises among tumor cells during treatment with vismodegib. There is clearly an urgent need to explore novel Smo antagonists with improved potency and efficacy. Through a scaffold hopping strategy, the authors have identified a series of novel tetrahydropyrido[4,3-d]pyrimidine derivatives, which exhibited effective inhibition of Hh signaling. Among them, compound I is three times more potent than vismodegib in the NIH3T3-GRE-Luc reporter gene assay. Compound I has lower m.p. and much greater solubility compared with vismodegib, resulting in linear PK profiles when dosed orally at 10, 30, and 100 mg/kg in rats. Furthermore, compound I showed excellent PK profiles with a 72% oral bioavailability in beagle dogs. Compound I demonstrated overall favorable in vitro safety profiles with respect to CYP isoform and hERG inhibition. Finally, compound I led to significant regression of s.c. tumor generated by primary Ptch1-deficient medulloblastoma cells in SCID mouse. In conclusion, tetrahydropyrido[4,3-d]pyrimidine derivatives represent a novel set of Smo inhibitors that could potentially be utilized to treat medulloblastoma and other Hh pathway related malignancies. The results came from multiple reactions, including the reaction of Azetidin-3-ol hydrochloride(cas: 18621-18-6Application In Synthesis 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.Application In Synthesis 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

COA of Formula: C3H8ClNOIn 2012 ,《Synthesis of the side chain of tebipenem pivoxil》 was published in Zhongguo Xinyao Zazhi. The article was written by Huang, Xiaoguang; Huang, Binge; Zhu, Shaoxuan. The article contains the following contents:

The side chain 1-(4,5-dihydrothiazol-2-yl) azetidine-3-thiol hydrochloride of tebipenem pivoxil was synthesized. 1-(4,5-Dihydrothiazol-2-yl) azetidine-3-thiol hydrochloride was prepared from 2-(methylthio)-4,5-dihydrothiazole by a 4-step process, i.e. successively reacted with 3-hydroxyazetidine hydrochloride, methanesulfonyl chloride, potassium ethanethioate and hydrolysis. The total yield of 1-(4,5-dihydrothiazol-2-yl) azetidine-3-thiol hydrochloride was 42%. This method increases the yield of 1-(4,5-dihydrothiazol-2-yl) azetidine-3-thiol hydrochloride, simplifies the process and decreases the cost. The results came from multiple reactions, including the reaction 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 2013,Gregory, Karen J.; Nguyen, Elizabeth D.; Reiff, Sean D.; Squire, Emma F.; Stauffer, Shaun R.; Lindsley, Craig W.; Meiler, Jens; Conn, P. Jeffrey published 《Probing the metabotropic glutamate receptor 5 (mGlu5) positive allosteric modulator (PAM) binding pocket: discovery of point mutations that engender a “”molecular switch”” in PAM pharmacology》.Molecular Pharmacology published the findings.Name: Azetidin-3-ol hydrochloride The information in the text is summarized as follows:

Pos. allosteric modulation of metabotropic glutamate receptor subtype 5 (mGlu5) is a promising novel approach for the treatment of schizophrenia and cognitive disorders. Allosteric binding sites are topog. distinct from the endogenous ligand (orthosteric) binding site, allowing for co-occupation of a single receptor with the endogenous ligand and an allosteric modulator. Neg. allosteric modulators (NAMs) inhibit and pos. allosteric modulators (PAMs) enhance the affinity and/or efficacy of the orthosteric agonist. The mol. determinants that govern mGlu5 modulator affinity vs. cooperativity are not well understood. Focusing on the modulators based on the acetylene scaffold, the authors sought to determine the mol. interactions that contribute to PAM vs. NAM pharmacol. Generation of a comparative model of the transmembrane-spanning region of mGlu5 served as a tool to predict and interpret the impact of mutations in this region. Application of an operational model of allosterism allowed for determination of PAM and NAM affinity estimates at receptor constructs that possessed no detectable radioligand binding as well as delineation of effects on affinity vs. cooperativity. Novel mutations within the transmembrane domain (TM) regions were identified that had differential effects on acetylene PAMs vs. 2-methyl-6-(phenylethynyl)-pyridine, a prototypical NAM. Three conserved amino acids (Y658, T780, and S808) and two non-conserved residues (P654 and A809) were identified as key determinants of PAM activity. Interestingly, the authors identified two point mutations in TMs 6 and 7 that, when mutated, engender a mode switch in the pharmacol. of certain PAMs. In the part of experimental materials, we found many familiar compounds, such as 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

COA of Formula: C3H8ClNOIn 2010 ,《Fatty acid amide hydrolase inhibitors. 2. Novel synthesis of sterically hindered azabenzhydryl ethers and an improved synthesis of VER-156084》 appeared in Tetrahedron Letters. The author of the article were Roughley, Stephen D.; Hart, Terance. The article conveys some information:

An improved synthesis of the fatty acid amide hydrolase (FAAH) inhibitor azetidinyl ether VER-156084 I was reported. The key step is a novel, environmentally benign etherification to form an unusual, highly hindered azabenzhydryl ether. The method is applied to a variety of primary and secondary alcs. In the experiment, the researchers used many compounds, for example, 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

The author of 《Design, Synthesis, and Evaluation of Reversible and Irreversible Monoacylglycerol Lipase Positron Emission Tomography (PET) Tracers Using a “”Tail Switching”” Strategy on a Piperazinyl Azetidine Skeleton》 were Chen, Zhen; Mori, Wakana; Deng, Xiaoyun; Cheng, Ran; Ogasawara, Daisuke; Zhang, Genwei; Schafroth, Michael A.; Dahl, Kenneth; Fu, Hualong; Hatori, Akiko; Shao, Tuo; Zhang, Yiding; Yamasaki, Tomoteru; Zhang, Xiaofei; Rong, Jian; Yu, Qingzhen; Hu, Kuan; Fujinaga, Masayuki; Xie, Lin; Kumata, Katsushi; Gou, Yuancheng; Chen, Jingjin; Gu, Shuyin; Bao, Liang; Wang, Lu; Collier, Thomas Lee; Vasdev, Neil; Shao, Yihan; Ma, Jun-An; Cravatt, Benjamin F.; Fowler, Christopher; Josephson, Lee; Zhang, Ming-Rong; Liang, Steven H.. And the article was published in Journal of Medicinal Chemistry in 2019. Related Products of 18621-18-6 The author mentioned the following in the article:

Monoacylglycerol lipase (MAGL) is a serine hydrolase that degrades 2-arachidonoylglycerol (2-AG) in the endocannabinoid system (eCB). Selective inhibition of MAGL has emerged as a potential therapeutic approach for the treatment of diverse pathol. conditions, including chronic pain, inflammation, cancer, and neurodegeneration. Herein, we disclose a novel array of reversible and irreversible MAGL inhibitors by means of “”tail switching”” on a piperazinyl azetidine scaffold. We developed a lead irreversible-binding MAGL inhibitor 8 and reversible-binding compounds 17 and 37, which are amenable for radiolabeling with 11C or 18F. [11C]8 ([11C]MAGL-2-11) exhibited high brain uptake and excellent binding specificity in the brain toward MAGL. Reversible radioligands [11C]17 ([11C]PAD) and [18F]37 ([18F]MAGL-4-11) also demonstrated excellent in vivo binding specificity toward MAGL in peripheral organs. This work may pave the way for the development of MAGL-targeted positron emission tomog. tracers with tunability in reversible and irreversible binding mechanisms. In the part of experimental materials, we found many familiar compounds, such as Azetidin-3-ol hydrochloride(cas: 18621-18-6Related Products 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.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 2013,Zhang, Lei; Villalobos, Anabella; Beck, Elizabeth M.; Bocan, Thomas; Chappie, Thomas A.; Chen, Laigao; Grimwood, Sarah; Heck, Steven D.; Helal, Christopher J.; Hou, Xinjun; Humphrey, John M.; Lu, Jiemin; Skaddan, Marc B.; McCarthy, Timothy J.; Verhoest, Patrick R.; Wager, Travis T.; Zasadny, Kenneth published 《Design and Selection Parameters to Accelerate the Discovery of Novel Central Nervous System Positron Emission Tomography (PET) Ligands and Their Application in the Development of a Novel Phosphodiesterase 2A PET Ligand》.Journal of Medicinal Chemistry published the findings.Synthetic Route of C3H8ClNO The information in the text is summarized as follows:

To accelerate the discovery of novel small mol. central nervous system (CNS) positron emission tomog. (PET) ligands, we aimed to define a property space that would facilitate ligand design and prioritization, thereby providing a higher probability of success for novel PET ligand development. Toward this end, we built a database consisting of 62 PET ligands that have successfully reached the clinic and 15 radioligands that failed in late-stage development as neg. controls. A systematic anal. of these ligands identified a set of preferred parameters for physicochem. properties, brain permeability, and nonspecific binding (NSB). These preferred parameters have subsequently been applied to several programs and have led to the successful development of novel PET ligands with reduced resources and timelines. This strategy is illustrated here by the discovery of the novel phosphodiesterase 2A (PDE2A) PET ligand 4-(3-[18F]fluoroazetidin-1-yl)-7-methyl-5-{1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}imidazo[5,1-f][1,2,4]triazine, [18F]PF-05270430 (5). In addition to this study using Azetidin-3-ol hydrochloride, there are many other studies that have used Azetidin-3-ol hydrochloride(cas: 18621-18-6Synthetic Route of C3H8ClNO) 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.Synthetic Route 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 1990,Archibald, T. G.; Baum, K.; Garver, L. C. published 《Synthesis of N-nitroazetidines》.Synthetic Communications published the findings.Recommanded Product: Azetidin-3-ol hydrochloride The information in the text is summarized as follows:

Direct nitrolysis of 3-substituted azetidine hydrochlorides with acetyl nitrate gives cyclic nitramines I (R = ONO2, O3SMe, CO2H). In the experiment, the researchers used Azetidin-3-ol hydrochloride(cas: 18621-18-6Recommanded Product: 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.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