- Protein kinase C modulators. Indolactams. 1. Efficient and flexible routes for the preparation of (-)-Indolactam V for use in the synthesis of analogsQuick, James; Saha, Bijali; Driedger, Paul E., Tetrahedron Letters, 1994, 35(46), 8549-52
Cas no 90365-57-4 ((-)-Indolactam V)
(-)-Indolactam V is a biologically active indole alkaloid that serves as a potent protein kinase C (PKC) activator. Its stereospecific structure enables selective interaction with PKC isoforms, making it a valuable tool for studying PKC-mediated signaling pathways in cellular and biochemical research. The compound exhibits high binding affinity and specificity, facilitating precise modulation of PKC activity in experimental settings. Its stability and well-characterized pharmacological profile allow for reproducible results in studies involving cell differentiation, proliferation, and tumor promotion. (-)-Indolactam V is particularly useful in mechanistic investigations of PKC-dependent processes, offering researchers a reliable compound for probing kinase-related biological functions.
(-)-Indolactam V structure
Product Name:(-)-Indolactam V
CAS No:90365-57-4
MF:C17H23N3O2
MW:301.383424043655
CID:804878
PubChem ID:329815323
Update Time:2025-06-06
(-)-Indolactam V Chemical and Physical Properties
Names and Identifiers
-
- (-)-Indolactam V
- (-)-Indolactam V ((-)-Ilv)
- (-)-Indolactam V,(2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one
- 3H-Pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one,1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-...
- Indolactam V
- (2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one
- (2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one (ACI)
- 3H-Pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-, [2S-(2R*,5R*)]- (ZCI)
- (-)-ILV
- BDBM50057511
- 5-(Hydroxymethyl)-1-methyl-2-(propan-2-yl)-2,5,6,8-tetrahydro-1H-[1,4]diazonino[7,6,5-cd]indol-3-ol
- ILV, (-)
- (S)-13-Hydroxymethyl-10-isopropyl-9-(S)-methyl-3,9,12-triaza-tricyclo[6.6.1.0*4,15*]pentadeca-1,4,6,8(15)-tetraen-11-one
- PDSP2_001364
- CS-5420
- 90365-57-4
- (10S,13S)-13-Hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0*4,15*]pentadeca-1,4(15),5,7-tetraen-11-one
- HB0002
- PDSP1_001380
- indolactam-V
- (2S,5S)-5-(hydroxymethyl)-2-isopropyl-1-methyl-4,5,6,8-tetrahydro-1H-[1,4]diazonino[7,6,5-cd]indol-3(2H)-one
- 3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-, (2S-(2R*,5R*))-
- ILV
- (10S,13S)-13-Hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0*4,15*]pentadeca-1,4,6,8(15)-tetraen-11-one
- SCHEMBL1278694
- Q27270189
- AT25351
- (2S,5S)-5-(hydroxymethyl)-2-isopropyl-1-methyl-1,2,5,6-tetrahydro-4H-[1,4]diazonino[7,6,5-cd]indol-3(8H)-one
- (2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one
- (2S,5S)-5-(hydroxymethyl)-1-methyl-2-(propan-2-yl)-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one
- 13-Hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0*4,15*]pentadeca-1,4,6,8(15)-tetraen-11-one(ILV)
- 3H-Pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one,1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-,(2S,5S)-
- CHEBI:192686
- (+-)-1,4,5,6-tetrahydro-1-methyl-5-(hydroxymethyl)-(2-1-methylethyl)-1H-pyrrolo[4,3,2-gh]1,4-benzodiazon-3-(2H)-one, 2-cis
- (10S,13S)-13-(hydroxymethyl)-9-methyl-10-propan-2-yl-3,9,12-triazatricyclo[6.6.1.04,15]pentadeca-1,4(15),5,7-tetraen-11-one
- NCGC00345085-01
- HSCI1_000195
- AKOS027326495
- Indolactum
- 8CIY9O1323
- CHEMBL27266
- C17H23N3O2
- 3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-, (2S,5S)-
- (-)-IndolactamV
- HY-12307
- 132341-58-3
- MS-24344
- BRN 4711877
- (+-)-IL-V
- UNII-8CIY9O1323
- hydroxymethyl-isopropyl-methyl-[?]one
- (-)-Indolactam V, >=96% (HPLC)
- INDOLACTAM V, (-)
- DTXSID60920432
- (+/-)-indolactum-V 13-Hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0*4,15*]pentadeca-1,4,6,8(15)-tetraen-11-one
- 13-Hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0*4,15*]pentadeca-1,4(15),5,7-tetraen-11-one
- (-)-Indolactam-V
-
- MDL： MFCD00151197
- Inchi： 1S/C17H23N3O2/c1-10(2)16-17(22)19-12(9-21)7-11-8-18-13-5-4-6-14(15(11)13)20(16)3/h4-6,8,10,12,16,18,21H,7,9H2,1-3H3,(H,19,22)/t12-,16-/m0/s1
- InChI Key： LUZOFMGZMUZSSK-LRDDRELGSA-N
- SMILES： CN1[C@@H](C(C)C)C(=O)N[C@H](CO)CC2=CNC3C2=C1C=CC=3
Computed Properties
- Exact Mass: 301.17900
- Monoisotopic Mass: 301.179
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 5
- Heavy Atom Count: 22
- Rotatable Bond Count: 2
- Complexity: 415
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 2
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Surface Charge: 0
- XLogP3: 2.3
- Topological Polar Surface Area: 68.4
Experimental Properties
- Color/Form: Not available
- Density: 1.166±0.06 g/cm3 (20 oC 760 Torr),
- Boiling Point: 584 °C at 760 mmHg
- Flash Point: 307 °C
- Refractive Index: 1.589
- Solubility: Slightly soluble (9 g/l) (25 o C),
- PSA: 68.36000
- LogP: 2.05570
- Solubility: Not available
(-)-Indolactam V Security Information
- Hazardous Material transportation number：NONH for all modes of transport
- WGK Germany：3
- RTECS：UY8547000
- Storage Condition：Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month
(-)-Indolactam V Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| MedChemExpress | HY-12307-10mM*1mLinDMSO |
(-)-Indolactam V |
90365-57-4 | 99.30% | 10mM*1mLinDMSO |
￥4376 | 2023-07-26 | |
| MedChemExpress | HY-12307-1mg |
(-)-Indolactam V |
90365-57-4 | 99.30% | 1mg |
￥1800 | 2024-05-24 | |
| MedChemExpress | HY-12307-5mg |
(-)-Indolactam V |
90365-57-4 | 99.30% | 5mg |
￥6600 | 2024-05-24 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | I275356-1mg |
(-)-Indolactam V |
90365-57-4 | ≥97% | 1mg |
￥2163.90 | 2023-09-02 | |
| Alichem | A199009226-5mg |
(-)-Indolactam V |
90365-57-4 | 98% | 5mg |
$494.34 | 2023-08-31 | |
| ChemScence | CS-5420-1mg |
(-)-Indolactam V |
90365-57-4 | 98.75% | 1mg |
$198.0 | 2022-04-26 | |
| ChemScence | CS-5420-5mg |
(-)-Indolactam V |
90365-57-4 | 98.75% | 5mg |
$726.0 | 2022-04-26 | |
| TRC | I577325-0.5mg |
(-)-Indolactam V |
90365-57-4 | 0.5mg |
$ 275.00 | 2022-06-04 | ||
| TRC | I577325-2.5mg |
(-)-Indolactam V |
90365-57-4 | 2.5mg |
$1539.00 | 2023-05-18 | ||
| TRC | I577325-5mg |
(-)-Indolactam V |
90365-57-4 | 5mg |
$2865.00 | 2023-05-18 |
(-)-Indolactam V Production Method
Production Method 1
Reaction Conditions
1.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran
Reference
Production Method 2
Reaction Conditions
1.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ; 5 h, rt
Reference
- Modular total synthesis of protein kinase C activator (-)-indolactam VHaynes-Smith, Jeremy; Diaz, Italia; Billingsley, Kelvin L., Organic Letters, 2016, 18(9), 2008-2011
Production Method 3
Reaction Conditions
1.1 Reagents: Chlorotrimethylsilane Solvents: Methanol , Dichloromethane ; 3 h, rt
1.2 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ; 1 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water
1.2 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ; 1 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water
Reference
- 11-Step Total Synthesis of Teleocidins B-1-B-4Nakamura, Hugh; Yasui, Kosuke; Kanda, Yuzuru; Baran, Phil S., Journal of the American Chemical Society, 2019, 141(4), 1494-1497
Production Method 4
Reaction Conditions
1.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ; 2 h, 23 °C
1.2 Reagents: Water ; cooled
1.2 Reagents: Water ; cooled
Reference
- Total syntheses of indolactam alkaloids (-)-Indolactam V, (-)-Pendolmycin, (-)-Lyngbyatoxin A, and (-)-Teleocidin A-2Fine Nathel, Noah F.; Shah, Tejas K.; Bronner, Sarah M.; Garg, Neil K., Chemical Science, 2014, 5(6), 2184-2190
Production Method 5
Reaction Conditions
Reference
- Synthesis of (-)-indolactam VMascal, Mark; Moody, Christopher J.; Slawin, Alexandra M. Z.; Williams, David J., Journal of the Chemical Society, 1992, (7), 823-30
Production Method 6
Reaction Conditions
1.1 Catalysts: Sodium bicarbonate
Reference
- Efficient syntheses and chemistry of indolactam-V and its analogsMasuda, Toshiya; Nakatsuka, Shinichi; Goto, Toshio, Agricultural and Biological Chemistry, 1989, 53(8), 2257-60
Production Method 7
Reaction Conditions
1.1 Reagents: Methyl iodide , Sodium bicarbonate Solvents: Methanol
Reference
- Synthesis of (-)-indolactam VMascal, Mark; Moody, Christopher J., Journal of the Chemical Society, 1988, (9), 589-90
Production Method 8
Reaction Conditions
1.1 Reagents: Magnesium , Ammonium chloride Solvents: Ethanol ; 2 d, rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt
Reference
- A concise total synthesis of (-)-indolactam VNoji, Toshiharu; Okano, Kentaro; Tokuyama, Hidetoshi, Tetrahedron, 2015, 71(23), 3833-3837
Production Method 9
Reaction Conditions
1.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ; 5 h, rt
1.2 Reagents: Water ; 0 °C
1.2 Reagents: Water ; 0 °C
Reference
- The Synthesis and Biological Evaluation of Indolactam AlkaloidsMendoza, Manuel; Eom, Ryan; Salas, Celeste; Haynes-Smith, Jeremy; Billingsley, Kelvin L., Synthesis, 2019, 51(23), 4443-4451
Production Method 10
Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 0 °C; 0 °C → rt; 5 h, rt
1.2 Reagents: Water ; rt
1.2 Reagents: Water ; rt
Reference
- Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer CellsStein, Jan; Stahn, Sonja; Neudoerfl, Joerg-M.; Sperlich, Julia; Schmalz, Hans-Guenther ; et al, ChemMedChem, 2018, 13(2), 147-154
Production Method 11
Reaction Conditions
1.1 Reagents: Oxygen Catalysts: (SP-5-41)-[1,3-Bis(2-methylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylen… Solvents: Ethyl acetate ; 1 atm, rt; 2 h, 70 °C
Reference
- Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused HeteroarenesKawauchi, Daichi; Noda, Kenta; Komatsu, Yoshiyuki; Yoshida, Kei; Ueda, Hirofumi; et al, Chemistry - A European Journal, 2020, 26(68), 15793-15798
Production Method 12
Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: Methanol
Reference
- Synthesis and stereochemistry of indolactam-V, an active fragment of teleocidins. Structural requirements for tumor-promoting activityEndo, Yasuyuki; Shudo, Koichi; Itai, Akiko; Hasegawa, Masashi; Sakai, Shinichiro, Tetrahedron, 1986, 42(21), 5905-24
Production Method 13
Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 30 min, 4 atm, rt
1.2 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; 0 °C; 3 h, 0 °C
1.3 Reagents: Diisopropylethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Tetrahydrofuran ; 48 h, rt
1.4 Reagents: Sodium cyanoborohydride Catalysts: Acetic acid Solvents: Acetonitrile ; 1 h, 0 °C
1.2 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; 0 °C; 3 h, 0 °C
1.3 Reagents: Diisopropylethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Tetrahydrofuran ; 48 h, rt
1.4 Reagents: Sodium cyanoborohydride Catalysts: Acetic acid Solvents: Acetonitrile ; 1 h, 0 °C
Reference
- Total synthesis of (-)-indolactam VXu, Zhengren; Zhang, Fengying; Zhang, Lihe; Jia, Yanxing, Organic & Biomolecular Chemistry, 2011, 9(7), 2512-2517
Production Method 14
Reaction Conditions
1.1 Reagents: NADH , Oxygen Catalysts: Catalase Solvents: Water ; 3 h, pH 8, rt
Reference
- Molecular basis for the P450-catalyzed C-N bond formation in indolactam biosynthesisHe, Fei; Mori, Takahiro; Morita, Iori; Nakamura, Hitomi; Alblova, Miroslava ; et al, Nature Chemical Biology, 2019, 15(12), 1206-1213
Production Method 15
Reaction Conditions
1.1 Reagents: NADPH Catalysts: Monooxygenase Solvents: Water ; pH 8
Reference
- Enzymatic Production of (-)-Indolactam V by LtxB, a Cytochrome P450 MonooxygenaseHuynh, Minh U.; Elston, Matthew C.; Hernandez, Nick M.; Ball, David B.; Kajiyama, Shin-ichiro; et al, Journal of Natural Products, 2010, 73(1), 71-74
(-)-Indolactam V Raw materials
- (-)-8-norindolactam V
- 1H-Pyrrolo[4,3,2-gh]-1,4-benzodiazonine-5-carboxylic acid, 2,3,4,5,6,8-hexahydro-1-methyl-2-(1-methylethyl)-3-oxo-, methyl ester, (2R,5S)-
- Butanamide, N-[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-3-methyl-2-(methylamino)-, (2S)-
(-)-Indolactam V Preparation Products
(-)-Indolactam V Related Literature
-
Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
-
Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
-
Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele Perego RSC Adv., 2016,6, 3617-3622
90365-57-4 ((-)-Indolactam V) Related Products
- 90365-56-3((+)-Indolactam V)
- 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
- 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
- 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
- 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
- 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
- 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
- 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
- 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
- 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
Recommended suppliers
PRIBOLAB PTE.LTD
Gold Member
Audited Supplier
CN Supplier
Reagent
Wuhan ChemNorm Biotech Co.,Ltd.
Gold Member
Audited Supplier
CN Supplier
Reagent
HANGZHOU BAIS CHEMICAL TECHNOLOGY CO., LTD.
Gold Member
Audited Supplier
CN Supplier
Reagent
Shenzhen Jianxing Pharmaceutical Technology Co., Ltd.
Gold Member
Audited Supplier
CN Supplier
Reagent
Hunan Well Medicine Synthesis Technology Co., Ltd.
Gold Member
Audited Supplier
CN Supplier
Reagent
