MedKoo Cat#: 585120 | Name: Olivacine

Description:

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

Olivacine is an alkaloid with antitumor and antileukemic activity isolated from Aspidosperma olivaceum.

Chemical Structure

Olivacine
Olivacine
CAS#484-49-1

Theoretical Analysis

MedKoo Cat#: 585120

Name: Olivacine

CAS#: 484-49-1

Chemical Formula: C17H14N2

Exact Mass: 246.1157

Molecular Weight: 246.31

Elemental Analysis: C, 82.90; H, 5.73; N, 11.37

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 #
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Synonym
Olivacine; Olivacin; SJ 2773
IUPAC/Chemical Name
1,5-Dimethyl-6H-pyrido(4,3-b)carbazole
InChi Key
ZIXGXMMUKPLXBB-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14N2/c1-10-12-7-8-18-11(2)14(12)9-15-13-5-3-4-6-16(13)19-17(10)15/h3-9,19H,1-2H3
SMILES Code
CC1=C2C(C(C)=NC=C2)=CC3=C1NC4=C3C=CC=C4
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
>3 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 246.31 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
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PubMed PMID: 29998591. 4: Schmidt U, Theumer G, Jäger A, Kataeva O, Wan B, Franzblau SG, Knölker HJ. Synthesis and Activity against Mycobacterium tuberculosis of Olivacine and Oxygenated Derivatives. Molecules. 2018 Jun 9;23(6). pii: E1402. doi: 10.3390/molecules23061402. PubMed PMID: 29890747; PubMed Central PMCID: PMC6100493. 5: Hibino S. [Synthetic Studies of Bioactive Heterocyclic Natural Products and Fused Heterocyclic Compounds Based on the Thermal Electrocyclic or Azaelectocyclic Reaction of 6π-Electron or Aza-6π-electron Systems]. Yakugaku Zasshi. 2016;136(4):607-48. doi: 10.1248/yakushi.15-00273. Review. Japanese. PubMed PMID: 27040345. 6: Zheng X, Lv L, Lu S, Wang W, Li Z. Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids. Org Lett. 2014 Oct 3;16(19):5156-9. doi: 10.1021/ol5025053. Epub 2014 Sep 15. PubMed PMID: 25222652. 7: Ramkumar N, Nagarajan R. Total synthesis of ellipticine quinones, olivacine, and calothrixin B. J Org Chem. 2014 Jan 17;79(2):736-41. doi: 10.1021/jo402593w. Epub 2014 Jan 6. PubMed PMID: 24372379. 8: Jasztold-Howorko R, Tylińska B, Biaduń B, Gebarowski T, Gasiorowski K. New pyridocarbazole derivatives. Synthesis and their in vitro anticancer activity. Acta Pol Pharm. 2013 Sep-Oct;70(5):823-32. PubMed PMID: 24147360. 9: dos Santos Torres ZE, Silveira ER, Rocha e Silva LF, Lima ES, de Vasconcellos MC, de Andrade Uchoa DE, Filho RB, Pohlit AM. Chemical composition of Aspidosperma ulei Markgr. and antiplasmodial activity of selected indole alkaloids. Molecules. 2013 May 29;18(6):6281-97. doi: 10.3390/molecules18066281. PubMed PMID: 23760029; PubMed Central PMCID: PMC6270234. 10: Rocha e Silva LF, Montoia A, Amorim RC, Melo MR, Henrique MC, Nunomura SM, Costa MR, Andrade Neto VF, Costa DS, Dantas G, Lavrado J, Moreira R, Paulo A, Pinto AC, Tadei WP, Zacardi RS, Eberlin MN, Pohlit AM. Comparative in vitro and in vivo antimalarial activity of the indole alkaloids ellipticine, olivacine, cryptolepine and a synthetic cryptolepine analog. Phytomedicine. 2012 Dec 15;20(1):71-6. doi: 10.1016/j.phymed.2012.09.008. Epub 2012 Oct 23. PubMed PMID: 23092722. 11: Santos AK, Machado LL, Bizerra AM, Monte FJ, Santiago GM, Braz-Filho R, Lemos TL. New indole alkaloid from Peschiera affinis (Apocynaceae). Nat Prod Commun. 2012 Jun;7(6):729-30. PubMed PMID: 22816293. 12: Schmidt AW, Reddy KR, Knölker HJ. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem Rev. 2012 Jun 13;112(6):3193-328. doi: 10.1021/cr200447s. Epub 2012 Apr 5. Review. PubMed PMID: 22480243. 13: Tylińska B, Jasztold-Howorko R, Mastalarz H, Kłopotowska D, Filip B, Wietrzyk J. Synthesis and structure-activity relationship analysis of new olivacine derivatives. Acta Pol Pharm. 2010 Sep-Oct;67(5):495-502. PubMed PMID: 20873417. 14: Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, Pinto AC, Sousa PM, Rezende CM, Epifanio Rde A. Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc. 2008 Sep;80(3):419-26. PubMed PMID: 18797794. 15: Bennasar ML, Roca T, Ferrando F. Regioselective 6-endo cyclizations of 2-indolylacyl radicals: total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine. J Org Chem. 2006 Feb 17;71(4):1746-9. PubMed PMID: 16468840. 16: Jasztold-Howorko R, Croisy A, Carrez D. An alternative way of the synthesis of 1-substituted 9-methoxy-5-methyl-6H-pyrido[4,3-b]carbazole derivatives. Acta Pol Pharm. 2005 May-Jun;62(3):207-12. PubMed PMID: 16193813. 17: Guillonneau C, Nault A, Raimbaud E, Léonce S, Kraus-Berthier L, Pierré A, Goldstein S. Cytotoxic and antitumoral properties in a series of new, ring D modified, olivacine analogues. Bioorg Med Chem. 2005 Jan 3;13(1):175-84. PubMed PMID: 15582462. 18: Jasztold-Howorko R, Croisy A, Carrez D, Jaroszewicz I, Nasulewicz A, Pełczyńska M, Opolski A. Synthesis, structure, and cytostatic properties of new olivacine derivatives. Arch Pharm (Weinheim). 2004 Nov;337(11):599-604. PubMed PMID: 15543533. 19: Pichard-Garcia L, Weaver RJ, Eckett N, Scarfe G, Fabre JM, Lucas C, Maurel P. The olivacine derivative s 16020 (9-hydroxy-5,6-dimethyl-N-[2-(dimethylamino)ethyl)-6H-pyrido(4,3-B)-carbazole-1-c arboxamide) induces CYP1A and its own metabolism in human hepatocytes in primary culture. Drug Metab Dispos. 2004 Jan;32(1):80-8. PubMed PMID: 14709624. 20: Vassal G, Merlin JL, Terrier-Lacombe MJ, Grill J, Parker F, Sainte-Rose C, Aubert G, Morizet J, Sévenet N, Poullain MG, Lucas C, Kalifa C. In vivo antitumor activity of S16020, a topoisomerase II inhibitor, and doxorubicin against human brain tumor xenografts. Cancer Chemother Pharmacol. 2003 May;51(5):385-94. Epub 2003 Mar 22. PubMed PMID: 12736760.