145075-81-6

Basic information

• Product Name: OSW-1
• Synonyms: OSW-1;16beta-[2-O-Acetyl-3-O-[2-O-(4-Methoxybenzoyl)-beta-D-xylopyranosyl)-alpha-L-arabinopyranosyloxy]-3b;16beta-[2-O-Acetyl-3-O-[2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl)-alpha-L-arabinopyranosyloxy]-3beta,17alpha-dihydroxycholest-5-en-22-one;(3β,16β)-16-[[2-O-Acetyl-3-O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-α-L-arabinopyranosyl]oxy]-3,17-dihydroxycholest-5-en-22-one
• CAS NO: 145075-81-6
• Molecular Formula: C₄₇H₆₈O₁₅
• Molecular Weight: 873.03
• Mol File: 145075-81-6.mol

Chemical Properties

• Boiling Point: 932.5 °C at 760 mmHg
• Flash Point: 267 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)
• PKA: 12.65±0.70(Predicted)
• CAS DataBase Reference: OSW-1(CAS DataBase Reference)
• NIST Chemistry Reference: OSW-1(145075-81-6)
• EPA Substance Registry System: OSW-1(145075-81-6)

Safety Data

• Hazardous Substances Data: 145075-81-6(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
OSW-1 is used as an antiviral agent for inhibiting the replication of a variety of enteroviruses, including coxsackievirus B3 (CVB3), hepatitis C virus (HCV), CVA9, and echovirus 2. It demonstrates potent antiviral activity with IC50s ranging from 2.4 to 9.4 nM and protects against CVA9 and echovirus 2 infection in HeLa cells when used at a concentration of 10 nM.
Used in Anticancer Applications:
OSW-1 is used as a selective cytotoxic agent for cancer cell lines, particularly HeLa and HEK293 cells. It inhibits the growth of these cells with GI50s of 0.33 and 0.22 nM, respectively, making it a promising candidate for cancer treatment.
Used in Pharmaceutical Research:
OSW-1 is used as a research tool for studying the role of OSBP and ORP4 in cellular processes, as well as their potential as therapeutic targets for various diseases, including cancer and viral infections.

InChI:InChI=1/C47H68O15/c1-24(2)8-15-34(50)25(3)47(55)37(21-33-31-14-11-28-20-29(49)16-18-45(28,5)32(31)17-19-46(33,47)6)60-44-41(59-26(4)48)39(36(52)23-58-44)62-43-40(38(53)35(51)22-57-43)61-42(54)27-9-12-30(56-7)13-10-27/h9-13,24-25,29,31-33,35-41,43-44,49,51-53,55H,8,14-23H2,1-7H3/t25-,29-,31+,32-,33-,35-,36+,37-,38+,39+,40-,41-,43+,44+,45+,46+,47-/m1/s1

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 18403-12-8 benzyl β-D-xylopyranoside 
• 219906-47-5 (3S,8R,9S,10R,13S,14S,16R,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-{(S)-1-[2-(3-methyl-butyl)-[1,3]dioxolan-2-yl]-ethyl}-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-16,17-diol 
• 321125-08-0 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate 
• 219906-55-5 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester 
• 219906-45-3 tert-Butyl-((3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-{(S)-1-[2-(3-methyl-butyl)-[1,3]dioxolan-2-yl]-ethyl}-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-diphenyl-silane 
• 219906-44-2 3β-(tert-butyldiphenylsiloxy)cholesta-5,16-dien-22-one 
• 219906-43-1 (22S)-3β-(tert-butyldiphenylsiloxy)cholesta-5,16-dien-22-ol 
• 321125-07-9 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate 
• 219906-42-0 (S)-2-[(3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propionaldehyde 
• 219906-41-9 (S)-2-[(3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propan-1-ol 
• 219906-50-0 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-benzyloxy-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester 

Downstream Products

• 1593111-61-5 C₅₈H₈₀N₄O₁₉S 
• 100-09-4 4-methoxybenzoic acid 
• 145075-83-8 3β,17α-dihydroxy-16β-[(O-β-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one 

Relevant articles and documents

A new synthesis of potent antitumor saponin OSW-1 via Wittig rearrangement

OSW-1 and its analogues in which thiophene ring was introduced at the side chain were synthesized employing Wittig rearrangement of 17E(20)-ethylidene-16α-(4′-methyl-2′-thienyl)methyloxy steroid. The synthesis required nine steps from the known 17E(20)-ethylidene-16α-hydroxy steroid in 15.6% overall yield.

OSW Saponins: Facile synthesis toward a new type of structures with potent antitumor activities

OSW saponins, featuring a 16β,17α-dihydroxycholest-22-one aglycon and an acylated β-D-xylopyranosyl-(1→3)-α-L- arabinopyranosyl residue attached to the 16-hydroxyl group, have recently been discovered from a group of lily plants, which show potent antitumor activities with a novel mechanism of action. This paper describes an aldol approach to the stereoselective construction of the 16α,17α-dihydroxycholest-22-one structure from 16α-hydroxy-5-androsten-17-ones and propionates. Elaboration of the aldol adducts toward OSW-1, involving installation of the isoamyl ketone side chain, inversion of the 16-hydroxyl configuration, and selective protection of the C22-oxy function, has been explored and accomplished. In particular, the present route was found convenient for the synthesis of OSW saponin analogues with a C22-ester side chain. Thus, the 23-oxa-analogue of OSW-1 (40) was prepared starting from the industrial dehydroisoandrosterone (1) in a linear eight-step sequence and in 26% overall yield. Analogues with a variety of modified side chains were prepared, via aldol condensation with propionates of varying length, thiopropionate, and acetate (for preparation of 68-75) or via aminolysis of the 22,16-lactone 26 (for preparation of the 23-N-analogues). Cross metathesis (CM) reaction was also found feasible for modification at the final stage from C22-allyl ester 70. Valuable structure-activity relationships (SAE), together with the practical synthetic approach, have thus been provided to set a new stage for further studies on this new type of antitumor structures.

Synthesis of analogues of a potent antitumor saponin OSW-1

A series of side chain analogues (5a-e), a 22-glycosylated isomer (10), and 16β-O-L-arabinosyl (13a) or 16β-O-D-xylosyl (13b) analogues of OSW-1 were synthesized. All analogues were found to be less cytotoxic against breast and endometrial cancer cell lines than the natural product.

Total synthesis of the anticancer natural product OSW-1

The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3β-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of α-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of α-halo vinyl ether chemistry developed in our laboratories.

Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity.

The potent antitumor agent OSW-1 was synthesized from the protected aglycone in different ways. It was proven that direct glycosylation of the aglycone in its hemiketal form could be achieved, affording the protected OSW-1 in a moderate yield. Alternatively, regioselective protection of the triol obtained by reduction of the aglycone, followed by glycosylation, deprotection and oxidation yielded the same OSW-1 derivative. The third approach to this compound consisted of glycosylation of the previously described lactol [Morzycki, J. W.; Gryszkiewicz, A. Polish J. Chem. 2001, 75, 983-989], reaction of the resulting aldehyde with a Grignard reagent, and oxidation. OSW-1 obtained on removal of the protective groups was identical with the natural product.

First total synthesis of an exceptionally potent antitumor saponin, OSW- 1

OSW-1 (1), an acylated disaccharide cholestane saponin from Ornithogalum saudersiae with exceptionally potent antitumor activity, was first synthesized from commercially available dehydroisoandrosterone, L-arabinose, and D-xylose in total 27 steps with the longest linear sequence of 14 steps and in 6% yield.