10184-70-0

Basic information

• Product Name: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)
• Synonyms: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL);21-Desacetyl Anecortave;17-Desacetyl Anecortave;17,21-Dihydroxypregna-4,9(11)-diene-3,20-dione;AL 4940
• CAS NO: 10184-70-0
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.44462
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 10184-70-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 231-233 °C(Solv: tetrahydrofuran (109-99-9))
• Boiling Point: 540.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)
• PKA: 12.52±0.60(Predicted)
• CAS DataBase Reference: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)(CAS DataBase Reference)
• NIST Chemistry Reference: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)(10184-70-0)
• EPA Substance Registry System: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)(10184-70-0)

Safety Data

• Hazardous Substances Data: 10184-70-0(Hazardous Substances Data)

Usage

Uses

17-Desacetyl Anecortave is a Anecortave Acetate (A637640). It displays glucocorticoid and mineralocorticoid receptor binding activities.

Synthetic route

anecortave (7753-60-8) → Anecortave (10184-70-0)

Conditions	Yield
With methanol; potassium carbonate
With potassium carbonate In methanol; water 1 h, room t., 50 min, 40 deg C;	5.33 g

21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregna-5,9(11)-dien-17-ol (428516-04-5) → Anecortave (10184-70-0)

Conditions	Yield
With sulfuric acid

Nicotinic acid (8S,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (119669-94-2) → Anecortave (10184-70-0)

Conditions	Yield
With potassium carbonate In methanol

anecortave (7753-60-8) → Anecortave (10184-70-0) + pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) + (10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one (10184-69-7) + pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one

Conditions	Yield
With Nocardioides simplex VKM Ac-2033D In phosphate buffer at 28℃; pH=7.5; Product distribution; Further Variations:; pH-values; Enzymatic reaction;

Nicotinic acid (8S,9R,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-9-chloro-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (108674-98-2) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: AgBF4 / acetone 2: K2CO3 / methanol View Scheme

Epicortisol (566-35-8) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: dann mit Methansulfonylchlorid 2: sodium acetate; acetic acid 3: K2CO3; methanol View Scheme

21-acetoxy-17-hydroxy-11α-methanesulfonyloxy-pregn-4-ene-3,20-dione (113862-93-4) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid 2: K2CO3; methanol View Scheme

21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol (74220-42-1) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride; pyridine 2: aqueous ethanol.H2SO4 View Scheme

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17,21-triol (76338-54-0) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine 2: phosphoryl chloride; pyridine 3: aqueous ethanol.H2SO4 View Scheme

methanolic potassium hydroxide + anecortave (7753-60-8) → Anecortave (10184-70-0)

Conditions	Yield
In methanol; dichloromethane

Anecortave (10184-70-0) → androst-4,9(11)-dien-3,17-dione (1035-69-4)

Conditions	Yield
With sodium bismuthate	87%
With manganese(IV) oxide In chloroform for 4h; Heating;	72.6%

Anecortave (10184-70-0) + acetic anhydride (108-24-7) → anecortave (7753-60-8)

Conditions	Yield
With pyridine

Anecortave (10184-70-0) + acetylating agent → anecortave (7753-60-8)

Anecortave (10184-70-0) → hydroxy-17β androstadiene-4,9(11) one-3,7 (2398-99-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C View Scheme

Anecortave (10184-70-0) → androstatriene-4,8,14 diol-3β,17β (105276-62-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 0.074 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 0.074 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 0.074 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme

Anecortave (10184-70-0) → methyl-14β, nor-18(13β) androstadiene-4,8 dione-3,17 (105276-63-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 44 percent / hydrofluoric acid / CH2Cl2 / 18 h / -15 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 44 percent / hydrofluoric acid / CH2Cl2 / 18 h / -15 °C View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 44 percent / hydrofluoric acid / CH2Cl2 / 18 h / -15 °C View Scheme

Anecortave (10184-70-0) → hydroxy-17β androstatriene-4,8,14 one-3 (105276-61-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h View Scheme
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h View Scheme

Anecortave (10184-70-0) → androstatriene-4,8,14 dione-3,17 (105369-18-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 0.008 g / Jones reagent / acetone / 0.17 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 0.008 g / Jones reagent / acetone / 0.17 h / 0 °C View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 0.008 g / Jones reagent / acetone / 0.17 h / 0 °C View Scheme

Anecortave (10184-70-0) → epoxy-9α,11α hydroxy-17β androstene-4 one-3 (105276-59-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

Anecortave (10184-70-0) → dihydroxy-9α,17β fluoro-11β androstene-4 one-3

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h View Scheme

Anecortave (10184-70-0) → acetoxy-17β androstatriene-4,8,14 one-3 (105306-04-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 0.035 g / pyridine View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 0.035 g / pyridine View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 0.035 g / pyridine View Scheme

butanoic acid anhydride (106-31-0) + Anecortave (10184-70-0) → 17α,21-dibutanoyloxy-pregna-4,9(11)-diene-3,20-dione (496942-70-2)

Conditions	Yield
With toluene-4-sulfonic acid In various solvent(s)

Anecortave (10184-70-0) → C21H30O4 + 17,21-dihydroxy-5α-pregn-9(11)-ene-3,20-dione

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon In ethanol for 6h; Reagent/catalyst; Reflux; Overall yield = 73 %; stereoselective reaction;	A n/a B n/a

Anecortave (10184-70-0) → (5β)-androst-9(11)-ene-3,17-dione (1093397-63-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon / ethanol / 6 h / Reflux 2: dipyridinium dichromate / dichloromethane / 48 h / 25 °C View Scheme

Anecortave (10184-70-0) → 17α-octadecanoyloxy-21-hydroxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2: Bacillus subtilis protease / tetrahydrofuran / 48 h / 45 °C / Enzymatic reaction 3: triphenylphosphine / dichloromethane / 0.5 h / 20 °C View Scheme

Anecortave (10184-70-0) → 17α-octadecanoyloxy-21-butanoyloxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2: Bacillus subtilis protease / tetrahydrofuran / 48 h / 45 °C / Enzymatic reaction 3: triphenylphosphine / dichloromethane / 0.5 h / 20 °C 4: methyl tributylammonium chloride / 2 h / 20 °C View Scheme

Anecortave (10184-70-0) → 17α-octadecanoyloxy-21-allylcarbonyloxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2: Bacillus subtilis protease / tetrahydrofuran / 48 h / 45 °C / Enzymatic reaction View Scheme

Anecortave (10184-70-0) + Allyl chloroformate (2937-50-0) → 17α-hydroxy-21-allylcarbonyloxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 0.5h;

Upstream product

• 7753-60-8 anecortave 
• 428516-04-5 21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregna-5,9⁽¹¹⁾-dien-17-ol 
• 76338-54-0 3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17,21-triol 
• 74220-42-1 21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol 
• 113862-93-4 21-acetoxy-17-hydroxy-11α-methanesulfonyloxy-pregn-4-ene-3,20-dione 
• 566-35-8 Epicortisol 
• 108674-98-2 Nicotinic acid (8S,9R,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-9-chloro-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 119669-94-2 Nicotinic acid (8S,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 

Downstream Products

• 2398-99-4 hydroxy-17β androstadiene-4,9(11) one-3,7 
• 7753-60-8 anecortave 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 

Relevant articles and documents

Microbial conversion of pregna-4,9(11)-diene-17α,21-diol-3,20-dione acetates by Nocardioides simplex VKM Ac-2033D

The conversion of pregna-4,9(11)-diene-17α,21-diol-3,20-dione 21-acetate (I) and 17,21-diacetate (VI) by Nocardioides simplex VKM Ac-2033D was studied. The major metabolites formed from I were identified as pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (II) and pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione (IV). Pregna-4,9(11)-diene-17α,21-diol-3,20-dione (III) and pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one (V) were formed in minorities. Biotransformation products formed from VI were pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17,21-diacetate (VII), pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (II), pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione (IV), pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17-acetate (VIII), pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one (V). The conversion pathways were proposed including 1(2)-dehydrogenation, deacetylation, 20β-reduction and non-enzymatic migration of acyl group from position 17 to 21. The conditions providing predominant accumulation of pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (II) from I and pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17-acetate (VIII) from VI in a short-term biotransformation were determined.

Selective Steroid Chlorinations Directed by Attached Pyridine Ester Templates

-

Non-hormonal steroid modulators of NF-κβ for treatment of disease

The present invention relates to compounds and methods which may be useful as treatments of diseases.

17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

The invention is the compound 17β-cyano-9α, 17α-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17α-halo silyl ethers (II).