50765-70-3

Basic information

• Product Name: (S)-1-TOSYLOXY-2,3-PROPANEDIOL
• Synonyms: (S)-1-TOSYL-GLYCEROL;(S)-1-TOSYLOXY-2,3-PROPANEDIOL;[S,(+)]-1-O-(p-Tolylsulfonyl)-L-glycerol;[S,(+)]-L-Glycerol 1-(p-toluenesulfonate);(S)-1,2,3-Propanetriol 4-Methylbenzenesulfonate;(S)-1-Tosyloxyglycerol;(S)-3-(p-Toluenesulfonyloxy)-1,2-propanediol;(S)-3-(Tosyloxy)-1,2-propanediol
• CAS NO: 50765-70-3
• Molecular Formula: C₁₀H₁₄O₅S
• Molecular Weight: 246.28
• Product Categories: Chiral Reagents;Aromatics;Sulfur & Selenium Compounds
• Mol File: 50765-70-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 54-58°C
• Boiling Point: 462.99°C at 760 mmHg
• Flash Point: 233.808°C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• PKA: 13.01±0.20(Predicted)
• CAS DataBase Reference: (S)-1-TOSYLOXY-2,3-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-TOSYLOXY-2,3-PROPANEDIOL(50765-70-3)
• EPA Substance Registry System: (S)-1-TOSYLOXY-2,3-PROPANEDIOL(50765-70-3)

Safety Data

• Hazardous Substances Data: 50765-70-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H14O5S/c1-8-2-4-10(5-3-8)16(13,14)15-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3/t9-/m0/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 15028-30-5 D-1-Benzyl-3-tosylglycerol 
• 139884-57-4 <(S)-2-(allyloxy)trimethylene> valerate p-toluenesulfonate 
• 138850-84-7 (S)-1-O-Tosyl-2-O-benzyl-3-O-methoxymethylglycerol 
• 104768-03-8 (-)-2,3-O-<(R)-Benzyliden>-5-O-(p-toluolsulfonyl)-D-ribonsaeure-γ-lacton 
• 51704-66-6 (+/-)-2,3-dihydroxypropyl tosylate 
• 40519-00-4 2,3-O-Isopropylidene-5-O-(p-tolylsulfonyl)-D-ribono-1,4-lactone 
• 4873-09-0 allyl tosylate 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 89174-50-5 (R)-glycerol acetonide 
• 141656-30-6 (R)-(+)-3-tosyloxypropane-1,2-diol dipropionate 
• 141656-36-2 Propionic acid (S)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester 
• 119970-97-7 (+)-5-O-(p-Toluolsulfonyl)-D-ribonsaeure-γ-lacton 
• 139884-58-5 <(S)-2-(allyloxy)-3-hydroxypropyl> p-toluenesulfonate 

Downstream Products

• 172587-60-9 (-)-(2S,cis)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol 
• 16495-04-8 (S)-1-O-benzyl-3-p-toluenesulfonyl-syn-glycerol 
• 134071-44-6 ((2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 
• 134071-44-6 ((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 
• 82966-35-6 (2S,4S)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-1,3-dioxolane 
• 82966-35-6 (2R,4S)-trans-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-1,3-dioxolane 

Relevant articles and documents

Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors

Itraconazole, a widely used antifungal drug, was found to possess antiangiogenic activity and is currently undergoing multiple clinical trials for the treatment of different types of cancer. However, it suffers from extremely low solubility and strong interactions with many drugs through inhibition of CYP3A4, limiting its potential as a new antiangiogenic and anticancer drug. To address these issues, a series of analogs in which the phenyl group is replaced with pyridine or fluorine-substituted benzene was synthesized. Among them the pyridine- and tetrazole-containing compound 24 has significantly improved solubility and reduced CYP3A4 inhibition compared to itraconazole. Similar to itraconazole, compound 24 inhibited the AMPK/mTOR signaling axis and the glycosylation of VEGFR2. It also induced cholesterol accumulation in the endolysosome and demonstrated binding to the sterol-sensing domain of NPC1 in a simulation study. These results suggested that compound 24 may serve as an attractive candidate for the development of a new generation of antiangiogenic drug.

Macrocyclic MCL-1 inhibitors and methods of use

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Repurposing the Clinically Efficacious Antifungal Agent Itraconazole as an Anticancer Chemotherapeutic

Itraconazole (ITZ) is an FDA-approved member of the triazole class of antifungal agents. Two recent drug repurposing screens identified ITZ as a promising anticancer chemotherapeutic that inhibits both the angiogenesis and hedgehog (Hh) signaling pathways. We have synthesized and evaluated first- and second-generation ITZ analogues for their anti-Hh and antiangiogenic activities to probe more fully the structural requirements for these anticancer properties. Our overall results suggest that the triazole functionality is required for ITZ-mediated inhibition of angiogenesis but that it is not essential for inhibition of Hh signaling. The synthesis and evaluation of stereochemically defined des-triazole ITZ analogues also provides key information as to the optimal configuration around the dioxolane ring of the ITZ scaffold. Finally, the results from our studies suggest that two distinct cellular mechanisms of action govern the anticancer properties of the ITZ scaffold.