Category: 57044-25-4

《Transition metal-free, base mediated one-pot approach for the construction of the benzo[b][1,4,5]oxathiazepine 1-oxide core》 was published in Organic & Biomolecular Chemistry in 2022. These research results belong to Banerjee, Arpita; Panda, Gautam. Computed Properties of C3H6O2 The article mentions the following:

Herein, a base mediated, transition metal-free intermol. epoxide ring opening by the nucleophilic attack of ortho-halogenated NH-sulfoximine followed by intramol. aromatic nucleophilic substitution (SNAr) for the synthesis of separable diastereomers of selected benzo[b][1,4,5]oxathiazepine 1-oxides I [R1 = Me, Et, cyclopentyl, etc.; R2 = CH:CH2, Ph, 2-naphthyl, etc.] was developed. Both C-N and C-O bonds were formed simultaneously in a single step. This strategy had a good substrate scope and required simple reaction conditions (room temperature) and cost-effective reagents, and showed good applicability for accessing sulfoximine analogs of benzoxathiazepine 1-oxide like bioactive skeletons. The absolute configurations of the separable major isomer I [R1 = n-Pr; R2 = CH2OCH2C6H5; stereo = R,R] minor isomer I [R1 = n-Pr; R2 = CH2OCH2C6H5; stereo = R,S] and single isomer II were confirmed by 2D NMR. On the other hand, the relative configuration of compound I [R1 = i-Pr; R2 = 4-ClC6H4] was assigned by 2D NMR along with X-ray crystal data anal. The results came from multiple reactions, including the reaction of (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Computed Properties of C3H6O2)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Computed Properties of C3H6O2

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The author of 《Exploration of the structure-activity relationship and druggability of novel oxazolidinone-based compounds as Gram-negative antibacterial agents》 were Ding, Shi; Ji, Jing-Chao; Zhang, Ming-Juan; Yang, Yu-She; Wang, Rui; Zhu, Xing-Long; Wang, Li-Hong; Zhong, Yi; Gao, Le; Lu, Man; Liu, Ju; Chen, Ye. And the article was published in Archiv der Pharmazie (Weinheim, Germany) in 2019. Synthetic Route of C3H6O2 The author mentioned the following in the article:

To gain further knowledge of the structure-activity relationship and druggability of novel oxazolidinone-based UDP-3-O-acyl-N-acetylglucosamine deacetylase (LpxC) inhibitors as Gram-neg. antibacterial agents, compounds containing the hydrophobic tails with different lengths and terminal substitutions were synthesized and their antibacterial activities against standard and clin. isolated Gram-neg. strains were evaluated. We summarized their structure-activity relationships and found that oxazolidinone-based compounds exhibited a narrower antibacterial spectrum compared with threonine-based compounds Furthermore, we parallelly compared the metabolic stabilities of the compounds with the classic threonine scaffold and the novel oxazolidinone scaffold in liver microsomes. The results indicated that the druggability of the oxazolidinone scaffold may be inferior to the classic threonine scaffold in the design of LpxC inhibitors. After reading the article, we found that the author used (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Synthetic Route of C3H6O2)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Synthetic Route of C3H6O2

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Name: (R)-Oxiran-2-ylmethanolOn October 15, 2019 ,《Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1,2,3-triazole side chain》 was published in European Journal of Medicinal Chemistry. The article was written by Qin, Yinhui; Teng, Yuetai; Ma, Ruixin; Bi, Fangchao; Liu, Zhiyang; Zhang, Panpan; Ma, Shutao. The article contains the following contents:

Macrolides are widely prescribed in clinic to treat various respiratory tract infections. However, due to their inappropriate use, the prevalence of macrolide-resistant strains among clin. isolates has become a concern for public health. Therefore, novel macrolides skeleton structures against resistant pathogens are badly needed. Thus, three series of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1,2,3-triazole side chain were designed and synthesized through creatively opening the ring of clarithromycin (CAM), expanding the ring properly, and introducing a suitable side chain of 1,2,3-triazole at the C12 and C13 positions; they were then evaluated for their antibacterial activity. The antibacterial results indicated that compounds I (R = Q, Q1, Q2) (II) possessed strong antibacterial activity against Staphylococcus aureus ATCC25923 (0.25 μg/mL) and Bacillus subtilis ATCC9372 (0.25 μg/mL). Furthermore, compounds I (R = Q3) (III) and I (R = Q4) (IV) were found to exhibit promising potent activity (8 μg/mL) against Streptococcus pneumonia AB11 expressing the ermB and mefA genes. In addition, the determination of min. bactericidal concentration (MBC) indicated that the most promising compounds II-IV were excellent bacteriostatic agents. The bactericidal curve showed that III exhibited antibacterial activity through bacteriostatic mechanism. Finally, II were confirmed to be non-toxic to MCF-7 breast cancer cells up to a concentration of 32 μg/mL in preliminary cytotoxicity assay. In summary, II-IV can serve as lead compounds to provide a new perspective for further structural optimization. In the part of experimental materials, we found many familiar compounds, such as (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Name: (R)-Oxiran-2-ylmethanol)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Name: (R)-Oxiran-2-ylmethanol

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Obst, Jon K.; Wang, Jun; Jian, Kunzhong; Williams, David E.; Tien, Amy H.; Mawji, Nasrin; Tam, Teresa; Yang, Yu Chi; Andersen, Raymond J.; Chi, Kim N.; Montgomery, Bruce; Sadar, Marianne D. published their research in ACS Pharmacology & Translational Science on December 13 ,2019. The article was titled 《Revealing Metabolic Liabilities of Ralaniten To Enhance Novel Androgen Receptor Targeted Therapies》.Name: (R)-Oxiran-2-ylmethanol The article contains the following contents:

Inhibition of the androgen receptor (AR) is the mainstay treatment for advanced prostate cancer. Ralaniten (formally EPI-002) prevents AR transcriptional activity by binding to its N-terminal domain (NTD) which is essential for transcriptional activity. Ralaniten acetate (EPI-506) the triacetate pro-drug of ralaniten, remains the only AR-NTD inhibitor to have entered clin. trials (NCT02606123). While well tolerated, the trial was ultimately terminated due to poor pharmacokinetic properties and resulting pill burden. Here we discovered that ralaniten was glucuronidated which resulted in decreased potency. Long-term treatment of prostate cancer cells with ralaniten results in upregulation of UGT2B enzymes with concomitant loss of potency. This has proven to be a useful model with which to facilitate the development of more potent second-generation AR-NTD inhibitors. Glucuronidated metabolites of ralaniten were also detected in the serum of patients in Phase 1 clin. trials. Therefore, we tested an analog of ralaniten (EPI-045) which was resistant to glucuronidation and demonstrated superiority to ralaniten in our resistant model. These data support that analogs of ralaniten designed to mitigate glucuronidation may optimize clin. responses to AR-NTD inhibitors. In addition to this study using (R)-Oxiran-2-ylmethanol, there are many other studies that have used (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Name: (R)-Oxiran-2-ylmethanol) was used in this study.

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Name: (R)-Oxiran-2-ylmethanol

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Computed Properties of C3H6O2On June 11, 2020, Fredo Naciuk, Fabricio; do Nascimento Faria, Jessica; Goncalves Eufrasio, Amanda; Torres Cordeiro, Artur; Bruder, Marjorie published an article in ACS Medicinal Chemistry Letters. The article was 《Development of Selective Steroid Inhibitors for the Glucose-6-phosphate Dehydrogenase from Trypanosoma cruzi》. The article mentions the following:

Chagas disease is a parasitic infection affecting millions of people across Latin America, imposing a dramatic socioeconomic burden. Despite the availability of drugs nifurtimox and benznidazole, lack of efficacy and incidence of side-effects prompt the identification of novel, efficient, and affordable drug candidates. To address this issue, one strategy could be probing the susceptibility of Trypanosoma parasites toward NADP-dependent enzyme inhibitors. Recently, steroids of the androstane group have been described as highly potent but nonselective inhibitors of parasitic glucose-6-phosphate dehydrogenase (G6PDH). In order to promote selectivity, we have synthesized and evaluated 26 steroid derivatives of epiandrosterone, e.g., I, in enzymic assays, whereby 17 compounds were shown to display moderate to high selectivity for T. cruzi over the human G6PDH. In addition, three compounds were effective in killing intracellular T. cruzi forms infecting rat cardiomyocytes. Altogether, this study provides new SAR data around G6PDH and further supports this target for treating Chagas disease. In the part of experimental materials, we found many familiar compounds, such as (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Computed Properties of C3H6O2)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Computed Properties of C3H6O2

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《Synthesis of phosphatidic acids via cobalt(salen) catalyzed epoxide ring-opening with dibenzyl phosphate》 was published in Organic & Biomolecular Chemistry in 2022. These research results belong to Andringa, Ruben L. H.; Jonker, Marijn; Minnaard, Adriaan J.. Category: alcohols-buliding-blocks The article mentions the following:

With a CoIII(salen)OTs catalyst, dibenzyl phosphate ring-opens a variety of terminal epoxides with excellent regio-selectively and yields up to 85%. The reaction is used in a highly efficient synthesis of enantiopure mixed-diacyl phosphatidic acids, including a photoswitchable phosphatidic acid mimic. After reading the article, we found that the author used (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Category: alcohols-buliding-blocks)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Category: alcohols-buliding-blocks

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Recommanded Product: (R)-Oxiran-2-ylmethanolOn May 15, 2019 ,《Potassium channel blocking 1,2-bis(aryl)ethane-1,2-diamines active as antiarrhythmic agents》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Kajanus, Johan; Antonsson, Thomas; Carlsson, Leif; Jurva, Ulrik; Pettersen, Anna; Sundell, Johan; Inghardt, Tord. The article conveys some information:

Herein, synthesis and optimization of a novel series of 1,2-diarylethane-1,2-diamines with selectivity for Kv1.5 over other potassium ion channels is presented. The effective refractory period in the right atrium (RAERP) in a rabbit PD model was investigated for a selection of potent and selective compounds with balanced DMPK properties. The most advanced compound I showed nanomolar potency in blocking Kv1.5 in human atrial myocytes and based on the PD data, the estimated dose to man is 700 mg/day. As previously reported, compound I efficiently converted AF to sinus rhythm in a dog disease model. The experimental process involved the reaction of (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Recommanded Product: (R)-Oxiran-2-ylmethanol)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Recommanded Product: (R)-Oxiran-2-ylmethanol

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Synthetic Route of C3H6O2On September 8, 2022 ,《Biological Effects of Modifications of the Englerin A Glycolate》 was published in ACS Medicinal Chemistry Letters. The article was written by Seenadera, Sarath P. D.; Long, Sarah A.; Akee, Rhone; Bermudez, Gabriela; Parsonage, Gregory; Strope, Jonathan; Peer, Cody; Figg, W. Douglas; Parker, Kathlyn A.; Beech, David J.; Beutler, John A.. The article contains the following contents:

Modifications at the glycolate moiety of englerin A were made to explore variations at the most sensitive site on the mol. for activity in the NCI 60 screen, wherein englerin A is highly potent and selective for renal cancer cells. Replacement of the glycolate by other functionalities as well as esterification of the glycolate hydroxyl yielded compounds which displayed excellent selectivity and potency compared with the natural product. TRPC4/5 ion channel experiments with five compounds showed delayed or reduced agonism with TRPC5, at much higher concentrations than englerin A. With TRPC4, these compounds all had no effect at 10 μM. The same compounds were not detectable in mouse serum after a single oral dose of 12.5 mg/kg. At 100 mg/kg p.o., no toxicity was observed, and blood levels were barely detectable. I.v. administration led to toxicity but at substantially lower doses than for englerin A.(R)-Oxiran-2-ylmethanol(cas: 57044-25-4Synthetic Route of C3H6O2) was used in this study.

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Synthetic Route of C3H6O2

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Wakamiya, Yuma; Ebine, Makoto; Matsumori, Nobuaki; Oishi, Tohru published an article on February 19 ,2020. The article was titled 《Total Synthesis of Amphidinol 3: A General Strategy for Synthesizing Amphidinol Analogues and Structure-Activity Relationship Study》, and you may find the article in Journal of the American Chemical Society.Reference of (R)-Oxiran-2-ylmethanol The information in the text is summarized as follows:

Amphidinol 3 (AM3) is a potent antifungal produced by the dinoflagellate Amphidinium klebsii. It was difficult to determine the absolute configuration of AM3 by using the scarce natural product due to the presence of numerous stereogenic centers on the acyclic carbon chain. Since the absolute configuration was partially determined on the basis of insufficient evidence, the originally proposed structure has been revised three times. Although recent progress on structure determination by computational anal. is remarkable, total synthesis is still the most reliable way to confirm structures. The first total synthesis of AM3 was achieved via expeditious assembly of three components in five steps, confirming the revised structure of AM3 after more than 20 years since its first discovery. The established synthetic route would be a general strategy for synthesizing amphidinol congeners. An artificial and simplified analog of AM3, which elicited antifungal activity comparable to that of AM3, was designed and synthesized. This is the first example of a biol. active artificial analog possessing a shorter polyol moiety, providing insight on the antifungal mode-of-action. After reading the article, we found that the author used (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Reference of (R)-Oxiran-2-ylmethanol)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Reference of (R)-Oxiran-2-ylmethanol

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The author of 《Chiral recognition of homochiral poly (amidoamine) dendrimers substituted with R- and S-glycidol by keratinocyte (HaCaT) and squamous carcinoma (SCC-15) cells in vitro》 were Malinga-Drozd, Malgorzata; Uram, Lukasz; Wrobel, Konrad; Wolowiec, Stanislaw. And the article was published in Polymers (Basel, Switzerland) in 2021. Reference of (R)-Oxiran-2-ylmethanol The author mentioned the following in the article:

The generation 2 and 3 poly(amidoamine) dendrimers (PAMAM G2 and G3) were converted into N-(2,3-dihydroxy)propyl derivatives by the addition of enantiomerically pure S- and R-glycidol. The homochiral dendrimers bind to HaCaT and SCC-15 cell membranes with an R/S glycidol enantioselectivity ratio of 1.5:1, as was quant. determined by fluorescence microscopy and visualized by confocal microscopy. Fully substituted G2 and G3 dendrimers were equipped with 32 and 64 N-(2,3-dihydroxy)propyl residues and showed effectively radial symmetry for homochiral derivatives in 13C NMR spectrum in contrary to analogs obtained by reaction with rac-glycidol. The sub-stoichiometric derivatives of G2 and G3 were also obtained in order to characterize them spectroscopically. The homochiral dendrimers were labeled with two different fluorescent labels, fluorescein, and rhodamine B, using their isothiocyanates to react with G2 and G3 followed by the addition of S- and R-glycidol. Obtained fluorescent derivatives were deficiently filled with N-(2,3-dihydroxy)propyl substituents due to steric hindrance imposed by the attached label. Nevertheless, these derivatives were used to determine their ability to bind to the cell membrane of human keratinocytes (HaCaT) and squamous carcinoma cells (SCC-15). Confocal microscopy images obtained from cells treated with variously labeled conjugates and fluorescence anal. with fluorescence reader allowed us to conclude that R-glycidol derivatives were bound and entered the cells preferentially, with higher accumulation in cancer cells. The G3 polyamidoamine (PAMAM)-based dendrimers were taken up more efficiently than G2 derivatives Moreover, S- and R-glycidol furnished dendrimers were highly biocompatible with no toxicity up to 300 Μ M concentrations, in contrast to the amine-terminated PAMAM analogs. The experimental process involved the reaction of (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Reference of (R)-Oxiran-2-ylmethanol)

(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Reference of (R)-Oxiran-2-ylmethanol

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