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Isoindoles and derivatives

Organic heterocyclic compounds that consist of a benzene ring fused with a pyrrole ring; these compounds are isomers of indole. Includes compounds that are derived from isoindoles.

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1

4-Nitrothalidomide, TRC

CAS: 19171-18-7 Molecular Formula: C13H9N3O6 Molecular Weight (g/mol): 303.23 Synonym: 2-(2,6-Dioxo-3-piperidinyl)-4-nitro-1H-isoindole-1,3(2H)-dione,2-(2,6-Dioxopiperidin-3-yl)-4-nitro-isoindole-1,3-dione,4-Nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione; IUPAC Name: 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione SMILES: [O-][N+](=O)c1cccc2C(=O)N(C3CCC(=O)NC3=O)C(=O)c12

CAS 19171-18-7
Molecular Weight (g/mol) 303.23
SMILES [O-][N+](=O)c1cccc2C(=O)N(C3CCC(=O)NC3=O)C(=O)c12
Synonym 2-(2,6-Dioxo-3-piperidinyl)-4-nitro-1H-isoindole-1,3(2H)-dione,2-(2,6-Dioxopiperidin-3-yl)-4-nitro-isoindole-1,3-dione,4-Nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;
IUPAC Name 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione
Molecular Formula C13H9N3O6
2

Thalidomide, TRC

CAS: 50-35-1 Molecular Formula: C13 H10 N2 O4 Molecular Weight (g/mol): 258.23 Synonym: Thalidomide,2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione,(±)-Thalidomide,1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline,3-Phthalimidoglutarimide,Celgene,Contergan,Distaval,K 17,Kevadon,Myrin,N-(2,6-Dioxo-3-piperidyl)phthalimide,N-Phthaloylglutamimide,NSC 527179,NSC 66847,Neurosedyn,Pantosediv,Pharmion,Quetimid,Sauramide,Sedalis,Sedoval,Softenil,Softenon,Suaramide,Synovir,Talimol,Talinol,Thaled,Thalomid,α-(N-Phthalimido)glutarimide,α-N-Phthalylglutaramide,α-Phthalimidoglutarimide IUPAC Name: 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione SMILES: O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1

CAS 50-35-1
Molecular Weight (g/mol) 258.23
SMILES O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
Synonym Thalidomide,2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione,(±)-Thalidomide,1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline,3-Phthalimidoglutarimide,Celgene,Contergan,Distaval,K 17,Kevadon,Myrin,N-(2,6-Dioxo-3-piperidyl)phthalimide,N-Phthaloylglutamimide,NSC 527179,NSC 66847,Neurosedyn,Pantosediv,Pharmion,Quetimid,Sauramide,Sedalis,Sedoval,Softenil,Softenon,Suaramide,Synovir,Talimol,Talinol,Thaled,Thalomid,α-(N-Phthalimido)glutarimide,α-N-Phthalylglutaramide,α-Phthalimidoglutarimide
IUPAC Name 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
Molecular Formula C13 H10 N2 O4
3

(S)-(-)-Thalidomide, TRC

CAS: 841-67-8 Molecular Formula: C13 H10 N2 O4 Molecular Weight (g/mol): 258.23 Synonym: 1H-Isoindole-1,3(2H)-dione, 2-[(3S)-2,6-dioxo-3-piperidinyl]- (9CI, ACI),1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (S)- (ZCI),2-[(3S)-2,6-Dioxo-3-piperidinyl]-1H-isoindole-1,3(2H)-dione (ACI),Phthalimide, N-(2,6-dioxo-3-piperidyl)-, L-(-)- (8CI),(-)-Thalidomide,(S)-(-)-Thalidomide,(S)-Thalidomide,2-[(3S)-2,6-Dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione,NSC 91730,S-(L)-Thalidomide,S-Lenalidomide IUPAC Name: 2-[(3S)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione SMILES: O=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1

CAS 841-67-8
Molecular Weight (g/mol) 258.23
SMILES O=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
Synonym 1H-Isoindole-1,3(2H)-dione, 2-[(3S)-2,6-dioxo-3-piperidinyl]- (9CI, ACI),1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (S)- (ZCI),2-[(3S)-2,6-Dioxo-3-piperidinyl]-1H-isoindole-1,3(2H)-dione (ACI),Phthalimide, N-(2,6-dioxo-3-piperidyl)-, L-(-)- (8CI),(-)-Thalidomide,(S)-(-)-Thalidomide,(S)-Thalidomide,2-[(3S)-2,6-Dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione,NSC 91730,S-(L)-Thalidomide,S-Lenalidomide
IUPAC Name 2-[(3S)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
Molecular Formula C13 H10 N2 O4
4

4-Nitro Lenalidomide, TRC

CAS: 827026-45-9 Molecular Formula: C13 H11 N3 O5 Molecular Weight (g/mol): 289.24 Synonym: 2,6-Piperidinedione, 3-(1,3-dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-,3-(1,3-Dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione,3-(4-Nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione,3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione,3-(4-Nitro-1-oxoisoindolin-2-yl)piperidin-2,6-dione,3-(4-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione,4-Nitro Lenalidomide IUPAC Name: 3-(7-nitro-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione SMILES: [O-][N+](=O)c1cccc2C(=O)N(Cc12)C3CCC(=O)NC3=O

CAS 827026-45-9
Molecular Weight (g/mol) 289.24
SMILES [O-][N+](=O)c1cccc2C(=O)N(Cc12)C3CCC(=O)NC3=O
Synonym 2,6-Piperidinedione, 3-(1,3-dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-,3-(1,3-Dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione,3-(4-Nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione,3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione,3-(4-Nitro-1-oxoisoindolin-2-yl)piperidin-2,6-dione,3-(4-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione,4-Nitro Lenalidomide
IUPAC Name 3-(7-nitro-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
Molecular Formula C13 H11 N3 O5
5

rac Lenalidomide-13C5, TRC

CAS: 1219332-91-8 Molecular Formula: C813C5H13N3O3 Molecular Weight (g/mol): 264.22 Synonym: Lenalidomide 13C5 SMILES: Nc1cccc2C(=O)N(Cc12)[13CH]3[13CH2][13CH2][13C](=O)N[13C]3=O

CAS 1219332-91-8
Molecular Weight (g/mol) 264.22
SMILES Nc1cccc2C(=O)N(Cc12)[13CH]3[13CH2][13CH2][13C](=O)N[13C]3=O
Synonym Lenalidomide 13C5
Molecular Formula C813C5H13N3O3
6

Apremilast, TRC

CAS: 608141-41-9 Molecular Formula: C22 H24 N2 O7 S Molecular Weight (g/mol): 460.5 Synonym: Acetamide, N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]-,N-[2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide,(S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione,(S)-N-[2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl]ethyl]-1,3-dioxoisoindolin-4-yl)acetamide,Apremilast,CC 10004,Otezla IUPAC Name: N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide SMILES: CCOc1cc(ccc1OC)[C@@H](CS(=O)(=O)C)N2C(=O)c3cccc(NC(=O)C)c3C2=O

CAS 608141-41-9
Molecular Weight (g/mol) 460.5
SMILES CCOc1cc(ccc1OC)[C@@H](CS(=O)(=O)C)N2C(=O)c3cccc(NC(=O)C)c3C2=O
Synonym Acetamide, N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]-,N-[2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide,(S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione,(S)-N-[2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl]ethyl]-1,3-dioxoisoindolin-4-yl)acetamide,Apremilast,CC 10004,Otezla
IUPAC Name N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
Molecular Formula C22 H24 N2 O7 S
7

Falipamil, TRC

CAS: 77862-92-1 Molecular Formula: C24H32N2O5 Molecular Weight (g/mol): 428.52 Synonym: 2-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindol-1-one,AQ-A 39; SMILES: COc1ccc(CCN(C)CCCN2Cc3cc(OC)c(OC)cc3C2=O)cc1OC

CAS 77862-92-1
Molecular Weight (g/mol) 428.52
SMILES COc1ccc(CCN(C)CCCN2Cc3cc(OC)c(OC)cc3C2=O)cc1OC
Synonym 2-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindol-1-one,AQ-A 39;
Molecular Formula C24H32N2O5
8

N,N'-Thiodiphthalimide (>90%), TRC

CAS: 7764-29-6 Molecular Formula: C16 H8 N2 O4 S Molecular Weight (g/mol): 324.31 Synonym: 2,2'-thiobis(isoindoline-1,3-dione),N,N'-thiodi Phthalimide,2,2'-Thiobis[1H-isoindole-1,3(2H)-dione],N,N'-Thiobisphthalimide IUPAC Name: 2-(1,3-dioxoisoindol-2-yl)sulfanylisoindole-1,3-dione SMILES: O=C1N(SN2C(=O)c3ccccc3C2=O)C(=O)c4ccccc14

CAS 7764-29-6
Molecular Weight (g/mol) 324.31
SMILES O=C1N(SN2C(=O)c3ccccc3C2=O)C(=O)c4ccccc14
Synonym 2,2'-thiobis(isoindoline-1,3-dione),N,N'-thiodi Phthalimide,2,2'-Thiobis[1H-isoindole-1,3(2H)-dione],N,N'-Thiobisphthalimide
IUPAC Name 2-(1,3-dioxoisoindol-2-yl)sulfanylisoindole-1,3-dione
Molecular Formula C16 H8 N2 O4 S
9

Des-acetyl Apremilast, TRC

CAS: 635705-72-5 Molecular Formula: C20H22N2O6S Molecular Weight (g/mol): 418.46 Synonym: 4-Amino-2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1H-isoindole-1,3(2H)-dione SMILES: CCOc1cc(ccc1OC)[C@@H](CS(=O)(=O)C)N2C(=O)c3cccc(N)c3C2=O

CAS 635705-72-5
Molecular Weight (g/mol) 418.46
SMILES CCOc1cc(ccc1OC)[C@@H](CS(=O)(=O)C)N2C(=O)c3cccc(N)c3C2=O
Synonym 4-Amino-2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1H-isoindole-1,3(2H)-dione
Molecular Formula C20H22N2O6S
10

3-Phthalimidopropanoyl Chloride (Technical Grade), TRC

CAS: 17137-11-0 Molecular Formula: C11H8ClNO3 Molecular Weight (g/mol): 237.64 Synonym: 3-Phthalimidopropionyl Chloride,3-Phthalimidoylpropionyl Chloride,Phthaloyl-beta-alanyl Chloride,beta-Phthalimidopropionic Acid Chloride,3-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)propionyl Chloride,3-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoyl Chloride IUPAC Name: 3-(1,3-dioxoisoindol-2-yl)propanoyl chloride SMILES: ClC(=O)CCN1C(=O)c2ccccc2C1=O

CAS 17137-11-0
Molecular Weight (g/mol) 237.64
SMILES ClC(=O)CCN1C(=O)c2ccccc2C1=O
Synonym 3-Phthalimidopropionyl Chloride,3-Phthalimidoylpropionyl Chloride,Phthaloyl-beta-alanyl Chloride,beta-Phthalimidopropionic Acid Chloride,3-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)propionyl Chloride,3-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoyl Chloride
IUPAC Name 3-(1,3-dioxoisoindol-2-yl)propanoyl chloride
Molecular Formula C11H8ClNO3
11

Folpet, TRC

CAS: 133-07-3 Molecular Formula: C9 H4 Cl3 N O2 S Molecular Weight (g/mol): 296.56 Synonym: 2-[(Trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione,Acryptane,Cosan T,Dipet,Faltan,Folnit,Folpan,Folpel,Ftalan,Fungitrol 11,Intercide TMP,N-[(Trichloromethyl)thio]phthalimide,Orthofaltan 50,Orthophaltan,Phaltan,Phaltane,Phthaltan,Ryl,Sanfol,Spolacid,Trifol,Vinicoli IUPAC Name: 2-(trichloromethylsulfanyl)isoindole-1,3-dione SMILES: ClC(Cl)(Cl)SN1C(=O)c2ccccc2C1=O

CAS 133-07-3
Molecular Weight (g/mol) 296.56
SMILES ClC(Cl)(Cl)SN1C(=O)c2ccccc2C1=O
Synonym 2-[(Trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione,Acryptane,Cosan T,Dipet,Faltan,Folnit,Folpan,Folpel,Ftalan,Fungitrol 11,Intercide TMP,N-[(Trichloromethyl)thio]phthalimide,Orthofaltan 50,Orthophaltan,Phaltan,Phaltane,Phthaltan,Ryl,Sanfol,Spolacid,Trifol,Vinicoli
IUPAC Name 2-(trichloromethylsulfanyl)isoindole-1,3-dione
Molecular Formula C9 H4 Cl3 N O2 S
12

BAY 41-2272, TRC

CAS: 256376-24-6 Molecular Formula: C20H17FN6 Molecular Weight (g/mol): 360.39 Synonym: BAY 41-2272,5-Cyclopropyl-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyrimidinamine IUPAC Name: 5-cyclopropyl-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-amine SMILES: Nc1nc(ncc1C2CC2)c3nn(Cc4ccccc4F)c5ncccc35

CAS 256376-24-6
Molecular Weight (g/mol) 360.39
SMILES Nc1nc(ncc1C2CC2)c3nn(Cc4ccccc4F)c5ncccc35
Synonym BAY 41-2272,5-Cyclopropyl-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyrimidinamine
IUPAC Name 5-cyclopropyl-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-amine
Molecular Formula C20H17FN6
13

4-Phthalimidobutyric Acid, TRC

CAS: 3130-75-4 Molecular Formula: C12H11NO4 Molecular Weight (g/mol): 233.22 Synonym: 4-Phthalimidoylbutyric Acid,N-Phthalyl-gamma-aminobutyric Acid,NSC 119133,Phthaloyl gamma-Aminobutyric Acid,gamma-Phthalimidobutyric Acid,1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanoic Acid,4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic Acid,4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyric Acid,4-(1,3-Dioxoisoindolin-2-yl)butanoic Acid,4-Phthalimidobutanoic Acid SMILES: OC(=O)CCCN1C(=O)c2ccccc2C1=O

CAS 3130-75-4
Molecular Weight (g/mol) 233.22
SMILES OC(=O)CCCN1C(=O)c2ccccc2C1=O
Synonym 4-Phthalimidoylbutyric Acid,N-Phthalyl-gamma-aminobutyric Acid,NSC 119133,Phthaloyl gamma-Aminobutyric Acid,gamma-Phthalimidobutyric Acid,1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanoic Acid,4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic Acid,4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyric Acid,4-(1,3-Dioxoisoindolin-2-yl)butanoic Acid,4-Phthalimidobutanoic Acid
Molecular Formula C12H11NO4
14

Dialifos, TRC

CAS: 10311-84-9 Molecular Formula: C14 H17 Cl N O4 P S2 Molecular Weight (g/mol): 393.85 Synonym: Phosphorodithioic acid, O,O-diethyl ester, S-ester with N-(2-chloro-1-mercaptoethyl)phthalimide (7CI,8CI),Phthalimide, N-(2-chloro-1-mercaptoethyl)-, S-ester with O,O-diethyl phosphorodithioate (8CI),Dialifor,Dialifos,Dialiphor,Dialiphos,Hercules 14503,O,O-Diethyl S-(2-chloro-1-phthalimidoethyl) phosphorodithioate,S-(2-Chloro-1-phthalimidoethyl) O,O-diethyl phosphorodithioate,Torak IUPAC Name: 2-(2-chloro-1-diethoxyphosphinothioylsulfanylethyl)isoindole-1,3-dione SMILES: CCOP(=S)(OCC)SC(CCl)N1C(=O)c2ccccc2C1=O

CAS 10311-84-9
Molecular Weight (g/mol) 393.85
SMILES CCOP(=S)(OCC)SC(CCl)N1C(=O)c2ccccc2C1=O
Synonym Phosphorodithioic acid, O,O-diethyl ester, S-ester with N-(2-chloro-1-mercaptoethyl)phthalimide (7CI,8CI),Phthalimide, N-(2-chloro-1-mercaptoethyl)-, S-ester with O,O-diethyl phosphorodithioate (8CI),Dialifor,Dialifos,Dialiphor,Dialiphos,Hercules 14503,O,O-Diethyl S-(2-chloro-1-phthalimidoethyl) phosphorodithioate,S-(2-Chloro-1-phthalimidoethyl) O,O-diethyl phosphorodithioate,Torak
IUPAC Name 2-(2-chloro-1-diethoxyphosphinothioylsulfanylethyl)isoindole-1,3-dione
Molecular Formula C14 H17 Cl N O4 P S2
15

Trehalulose, TRC

CAS: 51411-23-5 Molecular Formula: C12H22O11 Molecular Weight (g/mol): 342.3 Synonym: 1-O-alpha-D-Glucopyranosyl-D-fructose,1-O-alpha-D-Glucosylfructose,Mildear;Mildear 75,Trehalulose,Vitalose IUPAC Name: (3S,4R,5R)-3,4,5,6-tetrahydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one SMILES: OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

CAS 51411-23-5
Molecular Weight (g/mol) 342.3
SMILES OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Synonym 1-O-alpha-D-Glucopyranosyl-D-fructose,1-O-alpha-D-Glucosylfructose,Mildear;Mildear 75,Trehalulose,Vitalose
IUPAC Name (3S,4R,5R)-3,4,5,6-tetrahydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one
Molecular Formula C12H22O11