115314-17-5

Basic information

• Product Name: (R)-(-)-Glycidyl nosylate
• Synonyms: (R)-GLYCIDYL 3-NITROBENZENESULFONATE;(R)-(-)-GLYCIDYL-3-NOSYLATE;(R)-2,3-EPOXY-1-PROPYL-3-NITROBENZENESULFONATE;BENZENESULFONIC ACID, 3-NITRO-, (2R)-OXIRANYLMETHYL ESTER;3-NITROBENZENESULFONIC ACID (R)-GLYCIDYL ESTER;(2R)-(-)-GLYCIDYL-3-NITROBENZENESULFONATE;(2R)-(-)-Glycidyl-3-nitrobenzenesulphonate;(2R)-(-)-GLYCIDYL 3-NITROBENZENE-
• CAS NO: 115314-17-5
• Molecular Formula: C₉H₉NO₆S
• Molecular Weight: 259.24
• EINECS: 1308068-626-2
• Product Categories: chiral;CHIRAL COMPOUNDS;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 115314-17-5.mol

Chemical Properties

• Melting Point: 59-63 °C
• Boiling Point: 432.2 ºC at 760 mmHg
• Flash Point: 215.2 ºC
• Appearance: Slightly yellow/Crystalline Needles or Powder
• Density: 1.5881 (rough estimate)
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: (R)-(-)-Glycidyl nosylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-Glycidyl nosylate(115314-17-5)
• EPA Substance Registry System: (R)-(-)-Glycidyl nosylate(115314-17-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• RIDADR: UN 1325 4.1/PG II
• RTECS: DB7192000
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 115314-17-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-(-)-Glycidyl nosylate is used as a key intermediate in the synthesis of various organic compounds. Its application in this field is due to its ability to undergo a range of chemical reactions, such as nucleophilic substitution, addition, and elimination, which allows for the creation of diverse molecular structures with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(-)-Glycidyl nosylate is used as a starting material for the development of new drugs. Its unique chemical properties enable the synthesis of complex molecules with potential therapeutic effects, contributing to the discovery and innovation of novel pharmaceutical agents.
Used in Chemical Research:
(R)-(-)-Glycidyl nosylate is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic pathways. Its reactivity and structural features make it an ideal candidate for understanding the fundamental principles of organic chemistry and advancing the field.
Used in Material Science:
In the field of material science, (R)-(-)-Glycidyl nosylate is employed in the development of new materials with specific properties. Its incorporation into polymers, for instance, can lead to the creation of materials with enhanced mechanical, thermal, or electrical properties, depending on the desired application.

InChI:InChI=1/C9H9NO6S/c11-10(12)7-2-1-3-9(4-7)17(13,14)16-6-8-5-15-8/h1-4,8H,5-6H2/t8-/m1/s1

Upstream product

• 121-51-7 3-nitrobenzenesulphonyl chloride 
• 60456-23-7 (S)-oxiranemethanol 
• 152333-94-3 glycidyl nosylate 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 57044-25-4 (R)-oxiranemethanol 

Downstream Products

• 741719-53-9 4-{4-[(2R)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine 
• 119879-73-1 3-O-Hexadecyl-sn-glycerol 1-(3'-nitrobenzenesulfonate) 
• 119879-82-2 1-O-Hexadecyl-sn-glycerol 3-(3'-nitrobenzenesulfonate) 
• 157999-16-1 3,3'-Di-O-eicosamethylenedi-sn-glycerol 1,1'-bis(3'-nitrobenzenesulfonate) 
• 132059-11-1 R-<1-(2-amino-3-nitrophenoxy)>-2',3'-epoxypropane 
• 132059-13-3 S-<1-(2-amino-3-nitrophenoxy)>-2',3'-epoxypropane 
• 165657-99-8 (R)-1-(diphenylmethyl)-4-(2,3-epoxypropyl)piperazine 
• 127181-21-9 (1S,5R)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 
• 127181-22-0 (1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 
• 133715-45-4 (S)-(+)-1-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane 
• 203259-31-8 (R)-(-)-1-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane 
• 93744-17-3 (R)-(-)-3-(2-cyanophenoxy)-1,2-epoxypropane 
• 66966-19-6 (R)-1-(2'-allyloxyphenoxy)-2,3-epoxypropane 
• 6452-71-7 1-[2-(allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol 

Relevant articles and documents

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

AMINE-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS EHMT2 INHIBITORS, SALTS THEREOF, AND METHODS OF SYNTHESIS THEREOF

The present disclosure relates to amine-substituted heterocyclic compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating a disorder (e.g., cancer) by administering an amine-substituted heterocyclic heterocyclic compound disclosed herein or a pharmaceutical composition thereof to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.

Probing the Existence of a Metastable Binding Site at the β2-Adrenergic Receptor with Homobivalent Bitopic Ligands

Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous molecular dynamics studies on ligand binding to the β2-adrenergic receptor (β2AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacological characterization revealed ligands with similar potency and affinity, slightly increased β2/β1AR-selectivity, and/or substantially slower β2AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β2AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacological profiles of ligands.

Synthesis and biological evaluation of new simple indolic non peptidic HIV Protease inhibitors: The effect of different substitution patterns Dedicated to CINMPIS on the occasion of its 20th anniversary.

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 stereodefined 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 analysis allowed to identify several key features of the binding mode of such compounds to the protease.

Synthesis of the calcilytic ligand NPS 2143

(R)-3 (NPS 2143) is a negative allosteric modulator of the human calcium-sensing receptor (CaSR) and as such represents an important pharmacological tool compound for studying the CaSR. Herein, we disclose for the first time a complete experimental description, detailed characterisation and assessment of enantiomeric purity for (R)-3. An efficient, reproducible and scalable synthesis of (R)-3 that requires a minimum of chromatographic purification steps is presented. (R)-3 was obtained in excellent optical purity (er > 99:1) as demonstrated by chiral HPLC and the pharmacological profile for (R)-3 is in full accordance with that reported in the literature.

Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

The inhibition of ABC (ATP binding cassette) transporters is considered a powerful tool to reverse multidrug resistance. 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 analogues 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 multidrugresistance 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.

Synthesis and biological evaluation of novel small non-peptidic HIV-1 PIs: The benzothiophene ring as an effective moiety

Synthesis and biological evaluation of a new series of potential HIV-1 protease inhibitors incorporating different heterocycles are described. The variation of heteroatom in such molecules has displayed totally different biological activities and a benzothiophene containing inhibitor has shown high potency against wild type HIV-1 protease with IC50 = 60 nM, thanks to the lower desolvation penalty to be payed by such hydrophobic moiety.

NO-SSRIs: Nitric oxide chimera drugs incorporating a selective serotonin reuptake inhibitor

Hybrid nitrate drugs have been reported to provide NO bioactivity to ameliorate side effects or to provide ancillary therapeutic activity. Hybrid nitrate selective serotonin reuptake inhibitors (NO-SSRIs) were prepared to improve the therapeutic profile of this drug class. A synthetic strategy for use of a thiocarbamate linker was developed, which in the case of NO-fluoxetine facilitated hydrolysis to fluoxetine at pH 7.4 within 7 h. In cell culture, NO-SSRIs were weak inhibitors of the serotonin transporter; however, in the forced swimming task (FST) in rats, NO-fluoxetine demonstrated classical antidepressant activity. Comparison of NO-fluoxetine, with fluoxetine, and an NO-chimera nitrate developed for Alzheimer's disease (GT-1061) were made in the step through passive avoidance (STPA) test of learning and memory in rats treated with scopolamine as an amnesic agent. Fluoxetine was inactive, whereas NO-fluoxetine and GT-1061 both restored long-term memory. GT-1061 also produced antidepressant behavior in FST. These data support the potential for NO-SSRIs to overcome the lag in onset of therapeutic action and provide cotherapy of neuropathologies concomitant with depression.

METHODS AND COMPOSITIONS INVOLVING (S)-BUCINDOLOL

Disclosed is bucindolol substantially free of its R-stereoisomer. Also disclosed are pharmaceutical compositions that include bucindolol substantially free of its R-stereoisomer or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. Also disclosed are methods of treating a patient that involve administering to the patient a therapeutically effective amount of a composition of the present invention. Formula (I).

Chimeric Nitrate Esters and Use of the Same in a Treatment for Depression

Chimeric nitrate esters and their use in the treatment of depression are disclosed. The chimeric nitrate esters also are useful in the treatment of depression and comorbidity associated with aging.