3',5'-cyclic purine nucleoside phosphorothioates

Description:

3',5'-cyclic purine nucleoside phosphate analogues, where a phosphate oxygen has been exchanged for sulphur generating a chiral phosphorothioate. In 3',5'-cyclic nucleoside phosphorothioate, the oxygen atoms at the 3'- and 5'-positions of the ribose are part of the phosphorothioate group.

Ancestors:

Organic compounds ⮕ Nucleosides, nucleotides, and analogues ⮕ Nucleoside and nucleotide analogues ⮕ 3',5'-cyclic purine nucleoside phosphorothioates

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Sp-cAMPS
Moligand™ ?

Out of Stock Item #: S613668

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Technical Identifiers

IUPAC Name

6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol

SMILES

OC1C2OP(=S)(O)OCC2OC1n1cnc2c1ncnc2N

InChIKey
SMPNJFHAPJOHPP-UHFFFAOYSA-N

InChI

1S/C10H12N5O5PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)
Sp-8-pCPT-cAMPS
CAS: 129693-13-6 Formula: C₁₆H₁₄ClNaN₅O₅PS₂ Molecular Weight: 509.86

Out of Stock Item #: S338898

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IUPAC Name

(4aR,6R,7R,7aS)-6-[6-amino-8-(4-chlorophenyl)sulfanylpurin-9-yl]-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7show more

SMILES

C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3SC5=CC=C(C=C5)Cl)N)O)OP(=S)(O1)O

InChIKey
IVNQJYQKSYRLTE-IYKFWPKASA-N

InChI

1S/C16H15ClN5O5PS2/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(26-15)5-25-28(24,29)27-12/h1-4,6,9,11-12,15,23H,5H2,(H,24,29)show more

Synonyms
8-(4-Chlorophenylthio)adenosine-3',5'-cyclic monophosphorothioate
Rp-Adenosine 3′,5′-cyclic Monophosphorothioate, Sodium Salt
CAS: 73208-40-9 Formula: C₁₀H₁₁N₅O₅PS・Na Molecular Weight: 367.3

Moligand™ ?

Out of Stock Item #: R334410

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Technical Identifiers

IUPAC Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol;N,N-diethylethanamine

SMILES

CCN(CC)CC.C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O

InChIKey
OXIPZMKSNMRTIV-NVGWRVNNSA-N

InChI

1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6show more

Synonyms
RP-CAMPS
(S)-Adenosine, cyclic 3′,5′-(hydrogenphosphorothioate) triethylammonium
CAS: 71774-13-5 Formula: C₁₀H₁₂N₅O₅PS Molecular Weight: 345.27

≥98%

Out of Stock Item #: A339988

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IUPAC Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol

SMILES

C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O

InChIKey
SMPNJFHAPJOHPP-JOILOJCLSA-N

InChI

1S/C10H12N5O5PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)/t4-,6-,7-,10-,21?/m1/s1

Synonyms
(RP)-Camps | Rp-Adenosine 3',5'-cyclic Monophosphorothioate, Sodium Salt | p-Adenosine 3',5'-cyclic phosphorothiate |...
cAMPS-Rp, triethylammonium salt
CAS: 151837-09-1 Formula: C₁₀H₁₂N₅O₅PS.C₆H₁₅N Molecular Weight: 446.46

≥98%(HPLC)

Out of Stock Item #: C286882

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Technical Identifiers

IUPAC Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol;N,N-diethylethanamine

SMILES

CCN(CC)CC.C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O

InChIKey
OXIPZMKSNMRTIV-NVGWRVNNSA-N

InChI

1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6show more

Synonyms
(R)-Adenosine, cyclic 3',5'-(hydrogenphosphorothioate) triethylammonium

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