Neurological disorder treatment methods

1 . A method to treat a subject having, or subject to developing, a neurological disorder comprising administering to the subject an effective amount of

(i) 16α-bromoepiandrosterone hemihydrate, or

(ii) 16α-bromoepiandrosterone, 16β-bromoepiandrosterone, 16α-iodoepiandrosterone, 16β-iodoepiandrosterone, 3β,16α,17β-trihydroxyandrostane, 3β,16α,17β-trihydroxyandrostane, 3β,16α-dihydroxy-17-oxoandrostane, 3α,16α-dihydroxy-17-oxoandrostane, 3β,16β-dihydroxy-17-oxoandrostane, 3β,17β-dihydroxy-16α-flurorandrost-5-ene, 3β,17β-dihydroxyandrost-5-ene, 3α,17β-dihydroxyandrost-5-ene, 3β,17β-dimercaptoandrost-5-ene, 3α,17β-dimercaptoandrost-5-ene, 3β-mercapto-17β-hydroxyandrost-5-ene, 3α-mercapto-17β-hydroxyandrost-5-ene, 3β,17β-dihydroxyandrost-1,5-diene, 3α,17β-dihydroxyandrost-1,5-diene, 3β,16α,17β-trihydroxyandrost-1,5-diene, 3α,16α,17β-trihydroxyandrost-1,5-diene, 3β,7β,17β-trihydroxyandrost-5-ene, 3β-mercapto-7β,17β-dihydroxyandrost-5-ene, 3α,7β,17β-trihydroxyandrost-5-ene, 3β,16α,17β-trihydroxyandrost-5-ene, 3β,17β-dihydroxy-16α-flurorandrost-1,5-diene, 3β,7β,17β-trihydroxyandrost-1,5-diene, 3β-mercapto-7β,17β-dihydroxyandrost-1,5-diene or 3β,16α,17β-trihydroxyandrost-1,5-diene or a 2-oxa, 2-thia, 2-aza or 19-nor analog of any of these compounds or an ester, ether, carbonate, carbamate, thioacetal, thioester or thioether analog of any of these compounds, wherein the ester, ether, thioacetal, thioester or thioether is a C1-C50 moiety that is optionally substituted with 1, 2 or 3 independently selected —O—, —S—, —NH—, —C(O)—, ═O, ═S, —NH 2 , —C(O)OH, —O—C(O)—H, —OH, —SH, —NO 2 , —CN, —NHC(O)—, —C(O)NH—, —OC(O)—, —C(O)O—, —O-A8, —S-A8, —C(O)-A8, —OC(O)-A8, —C(O)O-A8, ═N—, —N═, ═N—OH, or halogen moieties or atoms where A8 is C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-4 alkyl-aryl, aryl or C 0-4 alkyl-C 2-9 heterocycle, or

(iii) a compound having the structure

wherein the dotted lines are optional double bonds and X is O or S;

R 1 is —H, —OH, —OR PR , —SH, —SR PR , —N 3 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 2 is —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 3 is —OH, OR PR , ═O, —SH, SR PR , ═S, ═CH 2 , —N 3 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 4 is —SH, —SR PR , ═S, —N(R PR ) 2 , a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, a thioether, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 5 and R 6 independently are —H, optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl;

R 7 is —CHR 10 —, —CHR 10 —CHR 10 —, —CHR 10 —CHR 10 —CHR 10 —, —CHR 10 —O—CHR 10 —, —CHR 10 —S—CHR 10 —, —CHR 10 —NR PR —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, wherein R 10 independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 8 is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 8 is absent, leaving a 5-membered ring, wherein R 10 independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 9 is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 9 is absent, leaving a 5-membered ring, wherein R 10 independently are —H, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, a thioester, an amide, an amino acid, a peptide, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

D is a heterocycle or a 4-, 5-, 6- or 7-membered ring that comprises saturated carbon atoms, wherein 1, 2 or 3 ring carbon atoms of the 4-, 5-, 6- or 7-membered ring are optionally independently substituted with —O—, —S— or —NR PR — or where 1, 2 or 3 hydrogen atoms of the heterocycle or 1 or 2 hydrogen atoms of the 4-, 5-, 6- or 7-membered ring are substituted with —OR PR , —SR PR , —N(R PR ) 2 , —O—Si—(R 3 ) 3 , —CN, —NO 2 , an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, a halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer, or, one more of the ring carbons are substituted with ═O or ═S, or D comprises two 5- or 6-membered rings, wherein the rings are fused or are linked by 1 or 2 bonds;

R PR independently or together are —H or a protecting group; and

R 13 independently are C 1 -C 6 alkyl.

2 . The method of claim 1 wherein R 1 , R 2 and R 4 independently are —OH, ═O—SH, ═S, an ester, an ether, a thioester or a thioether, R 3 is —H, —OH, ═O, —SH, ═S or —F and R 5 is —CH 3 or —CH 2 OH and R 6 is —H or —CH 3 .

3 . The method of claim 2 wherein R 7 and R 8 are —CH 2 —, R 9 is —O—, —S—, —CH 2 — or —CH═ and a double bond is present at the 5-6 position and optionally at the 1-2 position.

4 . The method of claim 3 wherein the neurological disorder is Alzheimer's Disease, Parkinson's Disease, schizophrenia or multiple sclerosis.

5 . The method of claim 4 wherein the compound is 16α-bromoepiandrosterone, 16β-bromoepiandrosterone, 16α-iodoepiandrosterone, 16β-iodoepiandrosterone, 3β,16α,17β-trihydroxyandrostane, 3α,16α,17β-trihydroxyandrostane, 3β,16α-dihydroxy-17-oxoandrostane, 3α,16α-dihydroxy-17-oxoandrostane, 3β,16β-dihydroxy-17-oxoandrostane, 3β,17β-dihydroxy-16α-flurorandrost-5-ene, 3β,17β-dihydroxyandrost-5-ene, 3α,17β-dihydroxyandrost-5-ene, 3β,17β-dimercaptoandrost-5-ene, 3α,17β-dimercaptoandrost-5-ene, 3β-mercapto-17β-hydroxyandrost-5-ene, 3α-mercapto-17β-hydroxyandrost-5-ene, 3β,17β-dihydroxyandrost-1,5-diene, 3α,17β-dihydroxyandrost-1,5-diene, 3β,16α,17β-trihydroxyandrost-1,5-diene, 3α,16α,17β-trihydroxyandrost-1,5-diene, 3β,7β,17β-trihydroxyandrost-5-ene, 3α,7β,17β-trihydroxyandrost-5-ene, 3β,16α,17β-trihydroxyandrost-5-ene, 3β,17β-dihydroxy-16α-flurorandrost-1,5-diene, 3β,7β,17β-trihydroxyandrost-1,5-diene or 3β,16α,17β-trihydroxyandrost-1,5-diene or a 2-oxa, 2-thia, 2-aza or 19-nor analog of any of these compounds or an ester, ether, carbonate, carbamate, thioacetal, thioester or thioether analog of any of these compounds, wherein the ester, ether, thioacetal, thioester or thioether is a C1-C50 moiety that is optionally substituted with 1, 2 or 3 independently selected —O—, —S—, —NH—, —C(O)—, ═O, ═S, —NH 2 , —C(O)OH, —O—C(O)—H, —OH, —SH, —NO 2 , —CN, —NHC(O)—, —C(O)NH—, —OC(O)—, —C(O)O—, —O-A8, —S-A8, —C(O)-A8, —OC(O)-A8, —C(O)O-A8, ═N—, —N═, ═N—OH, or halogen moieties or atoms where A8 is C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-4 alkyl-aryl, aryl or C 0-4 alkyl-C 2-9 heterocycle.

6 . The method of claim 4 wherein the compound is 16α-bromoepiandrosterone hemihydrate.

7 . A method to inhibit angiogenesis in a subject having a cancer or precancer, comprising administering to the subject an effective amount of

(i) 16α-hydroxyepiandrosterone, 3β,16α-dihydroxy-17-oxoandrostane, 3α,16α-dihydroxy-17-oxoandrostane, 3β,16α,17β-trihydroxyandrostane, 3α,16α,17β-trihydroxyandrostane, 3β,16α,17α-trihydroxyandrostane, 16β-bromoepiandrosterone, 16β-iodoepiandrosterone, 3β,17β-dimercaptoandrost-5-ene, 3α,17β-dimercaptoandrost-5-ene, 3β-mercapto-17β-hydroxyandrost-5-ene, 3α-mercapto-17β-hydroxyandrost-5-ene, 3β-mercapto-7β,17β-dihydroxyandrost-5-ene, 3α-mercapto-7β,17β-dihydroxyandrost-5-ene, 3β-hydroxy-7,17-dioxoandrost-5-ene, 3β-acetoxy-7,17-dioxoandrost-5-ene, 3β-propionoxy-7,17-dioxoandrost-5-ene, 3α,7α-dihydroxy-17-oxoandrost-5-ene, 3β,7β-dihydroxy-17-oxoandrost-5-ene, 3β-acetoxy-7α-hydroxy-17-oxoandrost-5-ene, 3β-acetoxy-7β-hydroxy-17-oxoandrost-5-ene, 3β-propionoxy-7α-hydroxy-17-oxoandrost-5-ene, 3β-propionoxy-7β-hydroxy-17-oxoandrost-5-ene or a 2-oxa, 2-aza or 2-thia analog of any of these compounds, or

(ii) 16α-bromoepiandrosterone hemihydrate, or

(iii) 16α-bromoepiandrosterone, 16α-iodoepiandrosterone, 16α-fluoroepiandrosterone, 16α-chloroepiandrosterone, 16β-bromoepiandrosterone, 16β-iodoepiandrosterone, 16β-fluoroepiandrosterone, 16β-chloroepiandrosterone, 3β,16α-dihydroxy-17-oxoandrostane, 3α,16α-dihydroxy-17-oxoandrostane, 3β,16α,17β-trihydroxyandrostane, 3α,16α,17β-trihydroxyandrostane, 3β-hydroxy-16α-bromo-17-oxo-5β-androstane, 3β-hydroxy-16α-iodo-17-oxo-5β-androstane, 3β-hydroxy-16α-fluoro-17-oxo-5β-androstane, 3β-hydroxy-16α-chloro-17-oxo-5β-androstane, 3β-hydroxy-16β-bromo-17-oxo-5β-androstane, 3β-hydroxy-16β-iodo-17-oxo-5β-androstane, 3β-hydroxy-16β-fluoro-17-oxo-5β-androstane, 3β-hydroxy-16β-chloro-17-oxo-5β-androstane, 3β,16α,17β-trihydroxyandrostane, 3α,16α,17β-trihydroxyandrostane, 3β,16α-dihydroxy-17-oxoandrostane, 3α,16α-dihydroxy-17-oxoandrostane, 3β,16β-dihydroxy-17-oxoandrostane, 3β,17β-dihydroxy-16α-flurorandrost-5-ene, 3α,17β-dihydroxyandrost-5-ene, 3β,17β-dihydroxy-7-oxoandrost-5-ene, 3α,17β-dihydroxy-7-oxoandrost-5-ene, 3β-hydroxy-7,17-dioxoandrost-5-ene, 3α-hydroxy-7,17-dioxoandrost-5-ene, 3β,17β-dihydroxyandrost-1,5-diene, 3α,17β-dihydroxyandrost-1,5-diene, 3β,16α,17β-trihydroxyandrost-1,5-diene, 3α,16α,17β-trihydroxyandrost-1,5-diene, 3β,7β,17β-trihydroxyandrost-5-ene, 3β,7β,17α-trihydroxyandrost-5-ene, 3α,7β,17β-trihydroxyandrost-5-ene, 3β,16α,17β-trihydroxyandrost-5-ene, 3β,17β-dihydroxy-16α-flurorandrost-1,5-diene, 3β,7β,17β-trihydroxyandrost-1,5-diene or 3β,16α,17β-trihydroxyandrost-1,5-diene or a 19-nor analog of any of these compounds or an ester, ether, thioacetal, thioester or thioether analog of any of these compounds, wherein the ester, ether, thioacetal, thioester or thioether is a C1-C50 moiety that is optionally substituted with 1, 2 or 3 independently selected —O—, —S—, —NH—, —C(O)—, ═O, ═S, —NH 2 , —C(O)OH, —O—C(O)—H, —OH, —SH, —NO 2 , —CN, —NHC(O)—, —C(O)NH—, —OC(O)—, —C(O)O—, —O-A8, —S-A8, —C(O)-A8, —OC(O)-A8, —C(O)O-A8, ═N—, —N═, ═N—OH, or halogen moieties or atoms where A8 is C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-4 alkyl-aryl, aryl or C 0-4 alkyl-C 2-9 heterocycle, or

(iv) a compound having the structure

wherein the dotted lines are optional double bonds and X is O or S;

R 1 is —OH, —OR PR , —SH, —SR PR , —N 3 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 2 is —OH, OR PR , ═O, —SH, SR PR , ═S, —N(R PR ) 2 , —N 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 3 is —OH, OR PR , ═O, —SH, SR PR , ═S, —N 3 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 4 is —SH, —SR PR , ═S, —N(R PR ) 2 , ═NOH, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, a thioether, a carbonate, a carbamate, a thioacetal, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 5 and R 6 independently are —H, optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl;

R 7 is —CHR 10 —, —CHR 10 —CHR 10 —, —CHR 10 —CHR 10 —CHR 10 —, —CHR 10 —O—CHR 10 —, —CHR 10 —S—CHR 10 —, —CHR 10 —NR PR —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, wherein R 10 independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 8 is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 8 is absent, leaving a 5-membered ring, wherein R 10 independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

R 9 is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 9 is absent, leaving a 5-membered ring, wherein R 10 independently are —H, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, a thioester, an amide, an amino acid, a peptide, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;

D is a heterocycle or a 4-, 5-, 6- or 7-membered ring that comprises saturated carbon atoms, wherein 1, 2 or 3 ring carbon atoms of the 4-, 5-, 6- or 7-membered ring are optionally independently substituted with —O—, —S— or —NR PR — or where 1, 2 or 3 hydrogen atoms of the heterocycle or 1 or 2 hydrogen atoms of the 4-, 5-, 6- or 7-membered ring are substituted with —OR PR , SR PR , N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl, a thioacyl, a carbonate, a carbamate, a thioacetal, a halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl moiety, optionally substituted heteroaryl, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer, or, one more of the ring carbons are substituted with ═O or ═S, or D comprises two 5- or 6-membered rings, wherein the rings are fused or are linked by 1 or 2 bonds;

R PR independently or together are —H or a protecting group; and

R 13 independently are C1-C6 alkyl.

8 . The method of claim 7 wherein R 1 , R 2 and R 4 independently are —OH, ═O, —SH, ═S, an ester, an ether, a thioester or a thioether and R 3 is —H, —Br or —Cl.

9 . The method of claim 8 wherein R 5 is —CH 3 or —CH 2 OH, R 6 is —H, —CH 3 or —CH 2 OH and R 7 and R 8 are —CH 2 —.

10 . The method of claim 9 wherein R 9 is —O—, —S—, —CH 2 — or —CH═ and a double bond is present at the 5-6 position and optionally at the 1-2 position.

11 . The method of claim 10 wherein R 1 is —OH, —O—C 2 H 5 , —O—CH 2 CH 2 CH 3 , —O—CH 2 CH 2 CH 2 CH 3 , —O—CH(CH 3 )CHCH 3 , —O—C(CH 3 ) 3 , —O—(CH 2 ) 4 CH 3 , —O—C(O)—CH 3 , —O—C(O)—C 2 H 5 , —O—C(O)—CH 2 CH 2 CH 3 , —O—C(O)—CH 2 CH 2 CH 2 CH 3 , —O—C(O)—CH 2 OH, —O—C(O)—CH 2 CH 2 OH, —O—C(O)—CH 2 CH 2 CH 2 OH, —O—C(O)—CH 2 SH, —O—C(O)—CH 2 CH 2 SH or —O—C(O)—CH 2 CH 2 CH 2 SH, R 2 is —OH, ═O, —SH or ═S and the compound has the structure

12 . The method of claim 7 wherein the compound is 16α-bromoepiandrosterone hemihydrate, 16α-hydroxyepiandrosterone, 3α,16α-dihydroxy-17-oxoandrostane, 3β,16α,17β-trihydroxyandrostane or 3α,16α,17β-trihydroxyandrostane.