Category: 115314-17-5

Baker, Jennifer R. published the artcileAmino Alcohol Acrylonitriles as Activators of the Aryl Hydrocarbon Receptor Pathway: An Unexpected MTT Phenotypic Screening Outcome, Quality Control of 115314-17-5, the publication is ChemMedChem (2020), 15(6), 490-505, database is CAplus and MEDLINE.

Lead (Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide, 1 showed MCF-7 GI₅₀=30 nM and 400-fold selective c.f. MCF10A (normal breast tissue). Acetamide moiety modification (13 a-g) to introduce addnl. hydrophobicity was favored with MCF-7 breast cancer cell activity enhanced at 1.3 nM. Other analogs were potent against the HT29 colon cancer cell line at 23 nM. Textbook SAR data was observed in the MCF-7 cell line, in an MTT assay, via the ortho (17 a), meta (17 b) and para (13 f). The amino alc. -OH moiety was pivotal, but no stereochem. preference noted. But, these data did not fit our homol. modeling expectations. Aberrant MTT ((3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide) screening results and metabolic interference confirmed by sulforhodamine B (SRB) screening. Interfering analogs resulted in 120 and 80-fold CYP1A1 and CYP1A2 amplification, with no upregulation of SULT1A1. This is consistent with activation of the AhR pathway. Piperidine per-deuteration reduced metabolic inactivation. 3-OH / 4-OH piperidine analogs showed differential MTT and SRB activity supporting MTT assay metabolic inactivation. Data supports piperidine 3-OH, but not the 4-OH, as a CYP substrate. This family of β-amino alc. substituted 3,4-dichlorophenylacetonitriles show broad activity modulated via the AhR pathway. By SRB anal. the most potent analog was 23 b, (Z)-3-(4-(3-(4-phenylpiperidin-1-yl)-2-hydroxypropoxy)phenyl)-2-(3,4-dichlorophenyl)-acrylonitrile.

ChemMedChem published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Quality Control of 115314-17-5.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Duncan, Kenneth W. published the artcileStructure and Property Guided Design in the Identification of PRMT5 Tool Compound EPZ015666, Computed Properties of 115314-17-5, the publication is ACS Medicinal Chemistry Letters (2016), 7(2), 162-166, database is CAplus and MEDLINE.

The recent publication of a potent and selective inhibitor of protein methyltransferase 5 (PRMT5) provides the scientific community with in vivo-active tool compound I (EPZ015666, GSK3235025) to probe the underlying pharmacol. of this key enzyme. Herein, the authors report the design and optimization strategies employed on an initial hit compound with poor in vitro clearance to yield in vivo tool compound I and an addnl. potent in vitro tool mol. II (GSK3203591).

ACS Medicinal Chemistry Letters published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Computed Properties of 115314-17-5.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Shin, Junhwa published the artcileAn Efficient New Route to Plasmenyl-type Lipids: Synthesis and Cytotoxicity of a Plasmenylcholine Analog of the Antitumor Ether Lipid ET-18-OMe, COA of Formula: C9H9NO6S, the publication is Journal of the American Chemical Society (2001), 123(3), 508-509, database is CAplus and MEDLINE.

Glycerolipid I has been prepared via a facile reaction sequence with use of an acrolein acetal derivative and 1-iodo-tridecane as precursors under Barbier-type reaction conditions. The observed regioselectivities and high Z:E ratios of the lithiated 4,4-di-tert-butylbiphenyl (DBB)-mediated coupling reaction are likely due to a lithiated allylic anion that undergoes stereoselective γ-coupling with electrophiles via lithium ion-acetal chelation. The resulting racemic I shows cytotoxic properties similar to the clin. relevant ATL analog 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine (ET-18-OMe); however, it is not presently known whether the cytotoxic mechanism for I is apoptotic in nature as it is for ET-18-OMe. Experiments designed to adapt this method for the preparation of plasmalogens and the pure R-I/S-I stereoisomers are in progress. Addnl. experiments aimed at probing the relative cytotoxicity of R-I, S-I, and racemic I, as well as the mechanism of cell death upon exposure to these ATL, are also planned.

Journal of the American Chemical Society published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C7H3Cl2F3O2S, COA of Formula: C9H9NO6S.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Barton, Donald L. published the artcilePreparation of positive inotropes using glycidyl derivatives: influence of metal ions and solvent on stereochemical outcome, Safety of (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Tetrahedron: Asymmetry (1992), 3(9), 1189-96, database is CAplus.

The choice of base and solvent has a dramatic effect on the attack of nitrogen nucleophiles on enantiomerically enriched glycidyl sulfonates I (R = 4-Me, 3-NO₂). Under the proper conditions attack can be largely limited to displacement of the sulfonate moiety thus retaining the original stereochem. Conditions were also noted where the initial attack resulted from epoxide opening. Subsequent attack of the intermediate alkoxide on the sulfonate group then yielded a product of opposite stereochem. The methodol. was applied to the syntheses of both enantiomers of carsatrin (II).

Tetrahedron: Asymmetry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Safety of (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zhang, Chufeng published the artcileDesign, synthesis and evaluation of novel 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as potent, selective and reversible Bruton’s tyrosine kinase (BTK) inhibitors for the treatment of rheumatoid arthritis, Computed Properties of 115314-17-5, the publication is European Journal of Medicinal Chemistry (2019), 121-143, database is CAplus and MEDLINE.

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives was designed and synthesized as reversible BTK inhibitors, and evaluated for their kinase selectivity, anti-proliferative activity against the B-cell lymphoma cell lines (Ramos, Jeko-1) and cell line BTK enhanced (Daudi) in vitro. Among them, pyrrolo[2,3-d]pyrimidine I exhibited the most excellent potency (IC₅₀ = 3.0 nM against BTK enzyme, 8.52 μM, 11.10 μM and 7.04 μM against Ramos, Jeko-1, Daudi cells, resp.), good kinase selectivity and inhibited BTK Y223 auto-phosphorylation and PLCγ2 Tyr1217 phosphorylation. Importantly, the compound I showed effective anti-arthritic effect on collagen-induced arthritis (CIA) model in vivo. 60 Mg/kg dose level once a day group displayed markedly reduced joint damage and cellular infiltration without any bone and cartilage morphol. change.

European Journal of Medicinal Chemistry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C16H24BF4Ir, Computed Properties of 115314-17-5.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Dhanoa, Daljit S. published the artcileThe synthesis of potent macrocyclic renin inhibitors, Related Products of esters-buliding-blocks, the publication is Tetrahedron Letters (1992), 33(13), 1725-8, database is CAplus.

An efficient synthesis of a novel class of potent macrocyclic renin inhibitors, exemplified by compounds I [R = Et, Bu, n-hexyl, morpholinomethyl, R¹ = Boc-Phe; R = Bu, morpholinomethyl, R¹ = (S)-Me₃CSO₂CH₂CH(CH₂Ph)CO; Boc = Me₃CO₂C], which involves the macrocyclization of glutamine derivative II as the key step, is described. The macrocyclic design of renin inhibitors I disclosed here incorporates (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutanoic acid as the transition-state isostere. Determination of stereochem. at the P₂‘ position of the more potent diastereomer of the 13-membered cyclic renin inhibitors I [R = morpholinomethyl, R¹ = PhCH₂O₂C, Boc-Phe, (S)-Me₃CSO₂CH₂CH(CH₂Ph)CO] is presented.

Tetrahedron Letters published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ohno, Tomoyasu published the artcileSynthesis and structure-activity relationship of 4-substituted benzoic acids and their inhibitory effect on the biosynthesis of fatty acids and sterols, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Archiv der Pharmazie (Weinheim, Germany) (2005), 338(4), 147-158, database is CAplus and MEDLINE.

The synthesis of 4-[3-(substituted phenyl)-2-oxo-5-oxazolidinyl]methoxybenzoic acids and their inhibitory effects on the biosynthesis of fatty acids and sterols is described. IC₅₀ values in vitro were 10^-6 and 10^-5 M, resp. Though the in vitro inhibitory activity of all these compounds toward sterol biosynthesis was inferior to that of pravastatin, several compounds had a stronger reducing effect in Sprague-Dawley (SD) rat on both, cholesterol (TC) and triglyceride (TG), than pravastatin and bezafibrate. The potent compounds were present at high concentrations in rat liver. The enantiomers of the potent racemic compound (4-[3-(4-bromo-2-fluorophenyl)-2-oxo-5-oxazolidinyl]methoxybenzoic acid) were prepared and their activity was examined in vivo and in vitro. In vivo, each enantiomer possessed more activity than the racemic compound Further, in Watanabe hereditable hyperlipidemic (WHHL) rabbit, optically active (R)-4-[3-(4-bromo-2-fluorophenyl)-2-oxo-5-oxazolidinyl]methoxybenzoic acid also potently reduced the effect of both TC and TG on serum levels, compared with pravastatin and bezafibrate.

Archiv der Pharmazie (Weinheim, Germany) published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Thompson, Andrew M. published the artcileRepositioning Antitubercular 6-Nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazoles for Neglected Tropical Diseases: Structure-Activity Studies on a Preclinical Candidate for Visceral Leishmaniasis, Product Details of C9H9NO6S, the publication is Journal of Medicinal Chemistry (2016), 59(6), 2530-2550, database is CAplus and MEDLINE.

6-Nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole derivatives were initially studied for tuberculosis within a backup program for the clin. trial agent pretomanid (PA-824). Phenotypic screening of representative examples against kinetoplastid diseases unexpectedly led to the identification of DNDI-VL-2098 as a potential first-in-class drug candidate for visceral leishmaniasis (VL). Addnl. work was then conducted to delineate its essential structural features, aiming to improve solubility and safety without compromising activity against VL. While the 4-nitroimidazole portion was specifically required, several modifications to the aryloxy side chain were well-tolerated e.g., exchange of the linking oxygen for nitrogen (or piperazine), biaryl extension, and replacement of Ph rings by pyridine. Several less lipophilic analogs displayed improved aqueous solubility, particularly at low pH, although stability toward liver microsomes was highly variable. Upon evaluation in a mouse model of acute Leishmania donovani infection,phenylpyridine derivative I stood out, providing efficacy surpassing that of the original preclin. lead.

Journal of Medicinal Chemistry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C7H8O3, Product Details of C9H9NO6S.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Lacivita, Enza published the artcilePrivileged scaffold-based design to identify a novel drug-like 5-HT₇ receptor-preferring agonist to target Fragile X syndrome, Computed Properties of 115314-17-5, the publication is European Journal of Medicinal Chemistry (2020), 112395, database is CAplus and MEDLINE.

Recent preclin. studies have shown that activation of the serotonin 5-HT₇ receptor has the potential to treat neurodevelopmental disorders such as Fragile X syndrome, a rare disease characterized by autistic features. With the aim to provide the scientific community with diversified drug-like 5-HT₇ receptor-preferring agonists, we designed a set of new long-chain arylpiperazines by exploiting structural fragments present in clin. approved drugs or in preclin. candidates (privileged scaffolds). The new compounds were synthesized, tested for their affinity at 5-HT₇ and 5-HT_1A receptors, and screened for their in vitro stability to microsomal degradation and toxicity. Selected compounds were characterized as 5-HT₇ receptor-preferring ligands, endowed with high metabolic stability and low toxicity. Compound 7g emerged as a drug-like 5-HT₇ receptor-preferring agonist capable to rescue synaptic plasticity and attenuate stereotyped behavior in a mouse model of Fragile X syndrome.

European Journal of Medicinal Chemistry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Computed Properties of 115314-17-5.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Fagerstroem, Alexandra published the artcileNew propranolol analogues: binding and chiral discrimination by cellobiohydrolase Cel7A, Recommanded Product: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Organic & Biomolecular Chemistry (2006), 4(16), 3067-3076, database is CAplus and MEDLINE.

Novel propranolol analogs have been designed and synthesized and their enantioselective binding to the cellulose degrading enzyme, Cel7A, has been evaluated. Affinity and enantioselectivity have been determined by capillary electrophoresis experiments Ligands with significantly improved affinity and selectivity have been obtained and an anal. of the results has led to insights concerning the relation between the changes in ligand structure and selectivity as well as affinity to the protein.

Organic & Biomolecular Chemistry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Recommanded Product: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics