Category: 115314-17-5

Shinagawa, Yuko published the artcileDiscovery of a Potent and Short-Acting Oral Calcilytic with a Pulsatile Secretion of Parathyroid Hormone, Product Details of C9H9NO6S, the publication is ACS Medicinal Chemistry Letters (2011), 2(3), 238-242, database is CAplus and MEDLINE.

Short-acting oral calcilytics, calcium-sensing receptor (CaSR) antagonists, have been considered as alternatives for parathyroid hormone (PTH), an injectable bone anabolic drug used in the treatment of osteoporosis. Previously, we identified aminopropandiol 1, which transiently stimulated endogenous PTH secretion in rats. However, the inhibition of cytochrome P 450 (CYP) 2D6 and the low bioavailability of 1 remain to be solved. Attempts to change the physicochem. properties of the highly lipophilic amine 1 by introduction of a carboxylic acid group as well as further structural modifications led to the discovery of the highly potent biphenylcarboxylic acid 15 (I), with a markedly reduced CYP2D6 inhibition and a significantly improved bioavailability. Compound 15 evoked a rapid and transient elevation of endogenous PTH levels in rats after oral administration in a dose-dependent manner at a dose as low as 1 mg/kg. The PTH secretion pattern correlated with the pharmacokinetic profile and agreed well with that of the exogenous PTH injection which exerts a bone anabolic effect.

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 C15H12O6, Product Details of C9H9NO6S.

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

Dittrich, Torsten published the artcileSynthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance, Application In Synthesis of 115314-17-5, the publication is Beilstein Journal of Organic Chemistry (2012), 1700-1704, database is CAplus and MEDLINE.

The inhibition of ABC (ATP binding cassette) transporters is considered a powerful tool to reverse multidrug resistance. (αR)-4-[(1Aα,6α,10bα)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]-α-[(5-quinolinyloxy)methyl]-1-piperazineethanol (Zosuquidar) featuring a difluorocyclopropyl-annulated dibenzosuberyl moiety has been found to be an inhibitor of the P-glycoprotein, one of the best-studied multidrug efflux pumps. Twelve 5-oxyisoquinoline derivatives, which are analogs of Zosuquidar wherein the dibenzosuberyl-piperazine moiety is replaced by either a diarylaminopiperidine or a piperidone-derived acetal or thioacetal group, have been synthesized as pure enantiomers. Their inhibitory power has been evaluated for the bacterial multidrug-resistance ABC transporter LmrCD and fungal Pdr5. Four of the newly synthesized compounds reduced the transport activity to a higher degree than Zosuquidar, being up to fourfold more efficient than the lead compound in the case of LmrCD and about two times better for Pdr5. The title compounds thus formed included a quinoline piperidineethanol derivative (I) and related substances. The synthesis of the target compounds was achieved using 5-[(2R)-2-oxiranylmethoxy]quinoline as a key intermediate.

Beilstein Journal of Organic 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, Application In Synthesis of 115314-17-5.

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

Bonini, C. published the artcileSynthesis and biological evaluation of new simple indolic non peptidic HIV Protease inhibitors: The effect of different substitution patterns, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Bioorganic & Medicinal Chemistry (2014), 22(17), 4792-4802, database is CAplus and MEDLINE.

New structurally simple indolic non peptidic HIV Protease inhibitors were synthesized from (S)-glycidol by regioselective methods. Following the concept of targeting the protein backbone, different substitution patterns were introduced onto the common stereo-defined isopropanolamine core modifying the type of functional group on the indole, the position of the functional group on the indole and the type of the nitrogen containing group (sulfonamides or perhydroisoquinoline), alternatively. The systematic study on in vitro inhibition activity of such compounds confirmed the general beneficial effect of the 5-indolyl substituents in presence of arylsulfonamide moieties, which furnished activities in the micromolar range. Preliminary docking anal. allowed to identify several key features of the binding mode of such compounds to the protease.

Bioorganic & 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, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

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

Sinsheimer, J. E. published the artcileThe genotoxicity of enantiomeric aliphatic epoxides, Recommanded Product: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Mutation Research, Genetic Toxicology Testing (1993), 298(3), 197-206, database is CAplus and MEDLINE.

The (R)- and (S)-optical isomers of 9 epoxides, benzyloxymethyloxirane, epichlorohydrin, glycidol, glycidyl 3-nitrobenzenesulfonate, glycidyl 4-nitrobenzoate, glycidyl tosylate, styrene oxide, glycidyl 1-naphthyl ether, and glycidyl 4-nitrophenyl ether, were compared for their in vivo and in vitro genotoxicity. Differences in mutagenicity between isomers were established with Salmonella TA100 for all the compounds While 13 of the isomers were genotoxic compared to a neg. control by chromosomal aberration measurements, only in the case of glycidyl 4-nitrobenzoate could a significant difference be found between isomers by this test. However, with sister chromatid exchange evaluations, differences were detected between the (R)- and (S)-isomers for all the pairs of compounds with the exception of those for benzyloxymethyloxirane and glycidyl 4-nitrophenyl ether. At least in part, differences in the patterns of genotoxicity among compounds can be related to their differences in reaction pathways.

Mutation Research, Genetic Toxicology Testing 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 C20H28B2O4S2, Recommanded Product: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

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

Ananth, Ramagopal published the artcileOptical purification of chiral glycidyl arenesulfonates, Application In Synthesis of 115314-17-5, the publication is Tetrahedron: Asymmetry (1995), 6(2), 317-20, database is CAplus.

The m.p. point phase diagrams of glycidyl tosylate (1), glycidyl 3-nitrobenzenesulfonate (2), and trans-3-methylglycidyl tosylate (3) have been investigated. Compounds 1 and 2 exhibit a more significant solid solution behavior in the terminal zones of the phase diagram than 3, and are therefore more difficult to enrich enantiomerically by recrystallizations The crystallization of 2 in ethanol is further complicated by polymorphism which can be followed by differential scanning calorimetry. The effects of these properties on the optical purification of 1–3 are discussed.

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, Application In Synthesis of 115314-17-5.

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

Guivisdalsky, Pedro N. published the artcileGlycidyl derivatives as chiral C₃ synthons. Ring opening catalyzed by boron trifluoride etherate, Quality Control of 115314-17-5, the publication is Journal of the American Chemical Society (1989), 111(8), 3077-9, database is CAplus.

The BF₃.OEt₂ mediated regio- and stereoselective opening reactions of (R)- and (S)-glycidyl arenesulfonates I (R = 4-MeC₆H₅SO₂, 3-O₂NC₆H₄SO₂) and tert-butyldiphenylsilyl ether I (R = Me₃CPh₂Si) with R¹XH [R¹ = PhCH₂, Me(CH)₁₅, oleyl, petroselinyl, X = O; R¹ = Ph, X = S] in CH₂Cl₂ or CHCl₃ is reported. BF₃.Et₂ was a more effective catalyst than other Lewis acids used previously for opening of glycidol, giving rise to (+)- and (-)-ROCH₂CH(OH)CH₂XR¹ (R, R¹, X = same as above) in good yield and high enantiomeric excess. Glycidyl arenesulfonates underwent attack exclusively at C(3), whereas the silyl ethers gave products resulting from C(3):C(2) attack in a ratio of 9:1. The BF₃.Et₂O catalyzed opening of glycidyl derivatives is a more convenient method for preparing suitably protected vic-diols than the previously described Ti-mediated opening the the parent glycidol.

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 C9H9NO6S, Quality Control of 115314-17-5.

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

Guivisdalsky, Pedro N. published the artcileAn efficient stereocontrolled route to both enantiomers of platelet activating factor and analogs with long-chain esters at C-2: saturated and unsaturated ether glycerolipids by opening of glycidyl arenesulfonates, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Journal of Organic Chemistry (1989), 54(19), 4643-8, database is CAplus.

Both enantiomers of various ether/ester glycerophosphocholines (R)-I and (S)-II (R¹ = e.g., hexadecyl, R² = pentadecyl, Me), including platelet activating factor I (R¹ = hexadecyl, R² = Me), were synthesized from arenesulfonate derivatives of glycidol (R)- and (S)-III (R³ = C₆H₄Me-4, C₆H₄NO₂-3) readily available in high enantiomeric purity. Regio- and stereospecific opening of (R)- or (S)-III with 1.0-1.4 equiv of long-chain saturated or unsaturated alc. using BF₃.Et₂O as catalyst in CH₂Cl₂ or CHCl₃ afforded (R)- and (S)-R³SO₃CH₂CH(OH)CH₂OR⁴ (IV; R³ = C₆H₄Me-4, C₆H₄NO₂-3; R⁴ = oleyl, petroselinyl, hexadecyl) in 73-83% yields and with the same very high optical purity of the parent glycidyl arenesulfonate (94-99% enantiomeric excess). For saturated alkyl/acyl I and II O-benzylation of IV was achieved with retention of the arenesulfonte group by using benzyl trifluoromethanesulfonate in the presence of excess 2,6-di-tert-butyl-4-methylpyridine; the C-2 hydroxyl of unsaturated O-alkyl IV is protected as the methoxymethyl ether under mild conditions in which the arenesulfonate group is retained. Displacement of the arenesulfonate group and introduction of the phosphocholine group to produce PAF analogs complete this route to chiral ether-ester phospholipids.

Journal of Organic 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, Name: (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

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

Shaw, Charles J. published the artcileA direct HPLC method for the resolution of glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate enantiomers, Quality Control of 115314-17-5, the publication is Journal of Pharmaceutical and Biomedical Analysis (1991), 9(10-12), 793-6, database is CAplus and MEDLINE.

The enantiomeric composition of glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate is obtained using an enantiomeric HPLC column. The chiral oxiranes were resolved on a cellulose carbamate column using a mobile phase of hexane/2-propanol. The method is simple, sensitive, and does not require derivatization.

Journal of Pharmaceutical and Biomedical Analysis 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 C7H8INO, Quality Control of 115314-17-5.

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

Furber, Mark published the artcileDiscovery and evolution of phenoxypiperidine hydroxyamide dual CCR3/H₁ antagonists. Part I, Safety of (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(24), 7702-7706, database is CAplus and MEDLINE.

The discovery of potent small mol. dual antagonists of the human CCR3 and H₁ receptors is described for the treatment of allergic diseases, for example, asthma and allergic rhinitis. Optimizing in vitro potency and metabolic stability, starting from a CCR1 lead compound, led to compound 20 with potent dual CCR3/H₁ activity and in vitro metabolic stability.

Bioorganic & 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, Safety of (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate.

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