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MedKoo Cat#: 463913 | Name: Isocryptolepine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Isocryptolepine is Potent Topoisomerase‑I Inhibitor.

Chemical Structure

Isocryptolepine
Isocryptolepine
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 463913

Name: Isocryptolepine

CAS#: unknown

Chemical Formula: C16H12N2

Exact Mass: 232.1000

Molecular Weight: 232.29

Elemental Analysis: C, 82.73; H, 5.21; N, 12.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Isocryptolepine;
IUPAC/Chemical Name
5-methyl-5H-indolo[3,2-c]quinoline
InChi Key
GLYLOCYYFNTVGX-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12N2/c1-18-10-13-11-6-2-4-8-14(11)17-16(13)12-7-3-5-9-15(12)18/h2-10H,1H3
SMILES Code
CN1C2=CC=CC=C2C3=NC4=CC=CC=C4C3=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 232.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Hsueh WY, Lee YE, Huang MS, Lai CH, Gao YS, Lin JC, Chen YF, Chang CL, Chou SY, Chen SF, Lu YY, Chang LH, Lin SF, Lin YH, Hsu PC, Wei WY, Huang YC, Kao YF, Teng LW, Liu HH, Chen YC, Yuan TT, Chan YW, Huang PH, Chao YT, Huang SY, Jian BH, Huang HY, Yang SC, Lo TH, Huang GR, Wang SY, Lin HS, Chuang SH, Huang JJ. Copper(I)-Catalyzed Nitrile-Addition/N-Arylation Ring-Closure Cascade: Synthesis of 5,11-Dihydro-6H-indolo[3,2-c]quinolin-6-ones as Potent Topoisomerase-I Inhibitors. J Med Chem. 2021 Jan 25. doi: 10.1021/acs.jmedchem.0c00727. Epub ahead of print. PMID: 33492141. 2: Chen C, Wang Y, Shi X, Sun W, Zhao J, Zhu YP, Liu L, Zhu B. Palladium- Catalyzed C-2 and C-3 Dual C-H Functionalization of Indoles: Synthesis of Fluorinated Isocryptolepine Analogues. Org Lett. 2020 Jun 5;22(11):4097-4102. doi: 10.1021/acs.orglett.0c01159. Epub 2020 May 27. PMID: 32459097. 3: Schendera E, Unkel LN, Huyen Quyen PP, Salkewitz G, Hoffmann F, Villinger A, Brasholz M. Visible-Light-Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines. Chemistry. 2020 Jan 2;26(1):269-274. doi: 10.1002/chem.201903921. Epub 2019 Nov 27. PMID: 31553081; PMCID: PMC6973160. 4: Li JC, Wang RX, Sun Y, Zhu JK, Hu GF, Wang YL, Zhou R, Zhao ZM, Liu YQ, Peng JW, Yan YF, Shang XF. Design, synthesis and antifungal activity evaluation of isocryptolepine derivatives. Bioorg Chem. 2019 Nov;92:103266. doi: 10.1016/j.bioorg.2019.103266. Epub 2019 Sep 14. PMID: 31542716. 5: Rujimongkon K, Mungthin M, Tummatorn J, Ampawong S, Adisakwattana P, Boonyuen U, Reamtong O. Proteomic analysis of Plasmodium falciparum response to isocryptolepine derivative. PLoS One. 2019 Aug 8;14(8):e0220871. doi: 10.1371/journal.pone.0220871. PMID: 31393938; PMCID: PMC6687117. 6: Wang N, Świtalska M, Wang L, Shaban E, Hossain MI, El Sayed IET, Wietrzyk J, Inokuchi T. Structural Modifications of Nature-Inspired Indoloquinolines: A Mini Review of Their Potential Antiproliferative Activity. Molecules. 2019 Jun 5;24(11):2121. doi: 10.3390/molecules24112121. PMID: 31195640; PMCID: PMC6600460. 7: Aksenov AV, Aksenov DA, Griaznov GD, Aksenov NA, Voskressensky LG, Rubin M. Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines. Org Biomol Chem. 2018 Jun 13;16(23):4325-4332. doi: 10.1039/c8ob00588e. PMID: 29808901. 8: Aksenov AV, Aksenov DA, Orazova NA, Aksenov NA, Griaznov GD, De Carvalho A, Kiss R, Mathieu V, Kornienko A, Rubin M. One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine. J Org Chem. 2017 Mar 17;82(6):3011-3018. doi: 10.1021/acs.joc.6b03084. Epub 2017 Mar 8. PMID: 28253622. 9: Mahajan PS, Humne VT, Tanpure SD, Mhaske SB. Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation. Org Lett. 2016 Jul 15;18(14):3450-3. doi: 10.1021/acs.orglett.6b01634. Epub 2016 Jul 5. PMID: 27377995. 10: Volvoikar PS, Tilve SG. Iodine-Mediated Intramolecular Dehydrogenative Coupling: Synthesis of N-Alkylindolo[3,2-c]- and -[2,3-c]quinoline Iodides. Org Lett. 2016 Mar 4;18(5):892-5. doi: 10.1021/acs.orglett.5b03392. Epub 2016 Feb 11. PMID: 26866309. 11: Aroonkit P, Thongsornkleeb C, Tummatorn J, Krajangsri S, Mungthin M, Ruchirawat S. Synthesis of isocryptolepine analogues and their structure- activity relationship studies as antiplasmodial and antiproliferative agents. Eur J Med Chem. 2015 Apr 13;94:56-62. doi: 10.1016/j.ejmech.2015.02.047. Epub 2015 Feb 26. PMID: 25747499. 12: Wang N, Wicht KJ, Imai K, Wang MQ, Anh Ngoc T, Kiguchi R, Kaiser M, Egan TJ, Inokuchi T. Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11. Bioorg Med Chem. 2014 May 1;22(9):2629-42. doi: 10.1016/j.bmc.2014.03.030. Epub 2014 Mar 26. PMID: 24721829. 13: Wang N, Świtalska M, Wu MY, Imai K, Ngoc TA, Pang CQ, Wang L, Wietrzyk J, Inokuchi T. Synthesis and in vitro cytotoxic effect of 6-amino-substituted 11H- and 11Me-indolo[3,2-c]quinolines. Eur J Med Chem. 2014 May 6;78:314-23. doi: 10.1016/j.ejmech.2014.03.038. Epub 2014 Mar 19. PMID: 24686018. 14: Bhowmik S, Pandey G, Batra S. Substituent-guided switch between C-H activation and decarboxylative cross-coupling during palladium/copper-catalyzed cascade reactions of 2-aminobenzoates with 2-haloarylaldehydes. Chemistry. 2013 Aug 5;19(32):10487-91. doi: 10.1002/chem.201301705. Epub 2013 Jun 20. PMID: 23788483. 15: Uchuskin MG, Pilipenko AS, Serdyuk OV, Trushkov IV, Butin AV. From biomass to medicines. A simple synthesis of indolo[3,2-c]quinolines, antimalarial alkaloid isocryptolepine, and its derivatives. Org Biomol Chem. 2012 Sep 28;10(36):7262-5. doi: 10.1039/c2ob25836f. PMID: 22814312. 16: Whittell LR, Batty KT, Wong RP, Bolitho EM, Fox SA, Davis TM, Murray PE. Synthesis and antimalarial evaluation of novel isocryptolepine derivatives. Bioorg Med Chem. 2011 Dec 15;19(24):7519-25. doi: 10.1016/j.bmc.2011.10.037. Epub 2011 Oct 20. PMID: 22055713. 17: Zsila F, Kámán J, Bogányi B, Józsvai D. Binding of alkaloids into the S1 specificity pocket of α-chymotrypsin: evidence from induced circular dichroism spectra. Org Biomol Chem. 2011 Jun 7;9(11):4127-37. doi: 10.1039/c0ob01221a. Epub 2011 Apr 11. PMID: 21483967. 18: Lavrado J, Moreira R, Paulo A. Indoloquinolines as scaffolds for drug discovery. Curr Med Chem. 2010;17(22):2348-70. doi: 10.2174/092986710791698521. PMID: 20491639. 19: Van Baelen G, Hostyn S, Dhooghe L, Tapolcsányi P, Mátyus P, Lemière G, Dommisse R, Kaiser M, Brun R, Cos P, Maes L, Hajós G, Riedl Z, Nagy I, Maes BU, Pieters L. Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues. Bioorg Med Chem. 2009 Oct 15;17(20):7209-17. doi: 10.1016/j.bmc.2009.08.057. Epub 2009 Sep 3. PMID: 19781948. 20: Grycová L, Dommisse R, Pieters L, Marek R. NMR determination of pKa values of indoloquinoline alkaloids. Magn Reson Chem. 2009 Nov;47(11):977-81. doi: 10.1002/mrc.2494. PMID: 19653253.