Ophiobolin A

Base Information

• Chemical Name: Ophiobolin A
• CAS No.: 4611-05-6
• Deprecated CAS: 1347-57-5,5843-70-9,11022-22-3,17046-71-8
• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.558
• Hs Code.: 2932190090
• European Community (EC) Number: 636-934-6
• ChEMBL ID: CHEMBL522808
• DSSTox Substance ID: DTXSID301017596
• Metabolomics Workbench ID: 28700
• Nikkaji Number: J14.566A
• Wikidata: Q27107581
• Mol file: 4611-05-6.mol

Synonyms:ophiobolin A

Chemical Property of Ophiobolin A

Chemical Property:

• Vapor Pressure: 6.91E-14mmHg at 25°C
• Melting Point: 182°C
• Refractive Index: 1.4460 (estimate)
• Boiling Point: 539.4°Cat760mmHg
• PKA: 13.84±0.70(Predicted)
• Flash Point: 177.8°C
• PSA: 63.60000
• Density: 1.14g/cm³
• LogP: 4.40800
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 400.26135963
• Heavy Atom Count: 29
• Complexity: 778

Purity/Quality:

99% ^*data from raw suppliers

Ophiobolin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(OC12CCC3(C2CC=C(C4C(C3)C(CC4=O)(C)O)C=O)C)C=C(C)C
• Isomeric SMILES: C[C@H]1C[C@@H](O[C@@]12CC[C@]3([C@H]2C/C=C(\[C@@H]4[C@H](C3)[C@](CC4=O)(C)O)/C=O)C)C=C(C)C
• General Description: Ophiobolin A is a fungal-derived sesterterpenoid with notable anticancer properties, attributed to its unique structural features, particularly the A/B-ring system. Simplified bicyclic derivatives of ophiobolin A have been synthesized to investigate its structure-activity relationship, revealing that key functional groups, such as the C3-hydroxy group and C6-stereochemistry, play a critical role in its cytotoxicity against cancer cells like MDA-MB-231 while maintaining selectivity over noncancerous cells (MCF-10A). These findings highlight its potential as a scaffold for developing targeted anticancer agents.

Technology Process of Ophiobolin A

There total 51 articles about Ophiobolin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(5α,7E,18R)-14,18-epoxyophiobola-7,19-diene-3,5,25-triol → Ophiobolin A (4611-05-6,24034-72-8,90411-19-1)

Guidance literature:

(5α,7E,18R)-14,18-epoxyophiobola-7,19-diene-3,5,25-triol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield:

2-[(2R,4S,5S,6R,7R)-7-[((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-78-4) → Ophiobolin A (4611-05-6,24034-72-8,90411-19-1)

Guidance literature:

Multi-step reaction with 23 steps

1.1: diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

6.1: diethyl ether / 0 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

8.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

9.2: -78 °C / Inert atmosphere

10.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / methanol; toluene / 50 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

12.1: pyridine; dmap / dichloromethane / 20 °C / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

14.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

15.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

16.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

17.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 110 °C / Inert atmosphere

18.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

19.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

20.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

20.2: -78 - 20 °C / Inert atmosphere

21.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

21.2: 20 °C / Inert atmosphere

22.1: naphthalene; lithium / tetrahydrofuran / -30 °C / Inert atmosphere

23.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

23.2: -78 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; naphthalene; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction / 20.1: Swern oxidation / 20.2: Swern oxidation / 21.1: Wittig reaction / 21.2: Wittig reaction / 23.1: Swern oxidation / 23.2: Swern oxidation;

DOI:10.1002/anie.201104447

Reference yield:

(1R,2S,3S,4S)-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-{[(2R,4S,5S,6R,7R)-2-tert-butyldiphenylsilyloxymethyl-6-(2-hydroxyethyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-1-methylcyclopentanol (1344673-92-2) → Ophiobolin A (4611-05-6,24034-72-8,90411-19-1)

Guidance literature:

Multi-step reaction with 22 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

5.1: diethyl ether / 0 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

7.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

8.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

8.2: -78 °C / Inert atmosphere

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / methanol; toluene / 50 °C / Inert atmosphere

10.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

11.1: pyridine; dmap / dichloromethane / 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

13.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

14.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

15.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

16.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 110 °C / Inert atmosphere

17.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

18.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

19.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

19.2: -78 - 20 °C / Inert atmosphere

20.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

20.2: 20 °C / Inert atmosphere

21.1: naphthalene; lithium / tetrahydrofuran / -30 °C / Inert atmosphere

22.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

22.2: -78 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; naphthalene; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Wittig reaction / 2.2: Wittig reaction / 19.1: Swern oxidation / 19.2: Swern oxidation / 20.1: Wittig reaction / 20.2: Wittig reaction / 22.1: Swern oxidation / 22.2: Swern oxidation;

DOI:10.1002/anie.201104447

upstream raw materials:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane

2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

(2R,3S,4S)-2-bromo-3-(tert-butyldimethylsilyl)oxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

(2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

Refernces

Pharmacophore-Directed Retrosynthesis Applied to Ophiobolin A: Simplified Bicyclic Derivatives Displaying Anticancer Activity

10.1021/acs.orglett.0c02938

The study focuses on the pharmacophore-directed retrosynthesis of ophiobolin A, a fungal-derived sesterterpenoid with significant anticancer activity. The researchers synthesized simplified bicyclic derivatives of ophiobolin A to explore their anticancer activity and understand the structure-activity relationship (SAR). Key chemicals used in the study include ophiobolin A, its congeners, and synthetic derivatives such as ketoaldehyde (±)-11, (±)-10, and (±)-38. These chemicals served to test the hypothesis that the cytotoxicity of ophiobolins originates from structural features of the A/B-ring system. The study employed various synthetic strategies, such as Michael addition, ring-closing metathesis, and selective protonation, to set the critical C6 stereocenter and form the cyclooctene ring. The synthesized derivatives were then tested for cytotoxicity against breast cancer cell lines (MDA-MB-231) and noncancerous cell lines (MCF-10A) to assess their anticancer activity and selectivity. The purpose of using these chemicals was to understand the minimal structural requirements for anticancer activity and to gain insights into the importance of specific structural features, such as the C3-hydroxy group and C6-stereochemistry, for bioactivity.

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