IUPAC/Chemical Name
1H-Carbazole-1,4(9H)-dione, 3-methyl-
InChi Key
XJTABSPWPMYLQX-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H9NO2/c1-7-6-10(15)12-11(13(7)16)8-4-2-3-5-9(8)14-12/h2-6,14H,1H3
SMILES Code
O=C(C=C1C)C(NC2=C3C=CC=C2)=C3C1=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
211.22
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.
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: McDonald JW, Miller JE, Kim M, Velu SE. An Expedient Synthesis of Murrayaquinone A via a Novel Oxidative Free Radical Reaction. Tetrahedron Lett. 2018 Feb 7;59(6):550-553. doi: 10.1016/j.tetlet.2018.01.007. Epub 2018 Jan 4. PMID: 29736091; PMCID: PMC5935454.
2: Mori-Quiroz LM, Dekarske MM, Prinkki AB, Clift MD. Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B. J Org Chem. 2017 Dec 1;82(23):12257-12266. doi: 10.1021/acs.joc.7b02101. Epub 2017 Nov 17. Erratum in: J Org Chem. 2018 Jun 1;83(11):6243. PMID: 29086565.
3: Takeya K, Itoigawa M, Furukawa H. Triphasic inotropic response of guinea-pig papillary muscle to murrayaquinone-A isolated from Rutaceae. Eur J Pharmacol. 1989 Oct 4;169(1):137-45. doi: 10.1016/0014-2999(89)90825-x. PMID: 2599008.
4: Suematsu N, Ninomiya M, Sugiyama H, Udagawa T, Tanaka K, Koketsu M. Synthesis of carbazoloquinone derivatives and their antileukemic activity via modulating cellular reactive oxygen species. Bioorg Med Chem Lett. 2019 Aug 15;29(16):2243-2247. doi: 10.1016/j.bmcl.2019.06.038. Epub 2019 Jun 20. PMID: 31253531.
5: Itoigawa M, Kashiwada Y, Ito C, Furukawa H, Tachibana Y, Bastow KF, Lee KH. Antitumor agents. 203. Carbazole alkaloid murrayaquinone A and related synthetic carbazolequinones as cytotoxic agents. J Nat Prod. 2000 Jul;63(7):893-7. doi: 10.1021/np000020e. PMID: 10924160.
6: Kaliyaperumal SA, Banerjee S, U K SK. Palladium mediated intramolecular multiple C-X/C-H cross coupling and C-H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A. Org Biomol Chem. 2014 Aug 28;12(32):6105-13. doi: 10.1039/c4ob00493k. PMID: 24881674.
7: Chakraborty B, Chakraborty S, Saha C. Antibacterial Activity of Murrayaquinone A and 6-Methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione. Int J Microbiol. 2014;2014:540208. doi: 10.1155/2014/540208. Epub 2014 May 20. PMID: 24963299; PMCID: PMC4055288.
8: Hagiwara H, Choshi T, Nobuhiro J, Fujimoto H, Hibino S. Novel syntheses of murrayaquinone A and furostifoline through 4-oxygenated carbazoles by allene- mediated electrocyclic reactions starting from 2-chloroindole-3-carbaldehyde. Chem Pharm Bull (Tokyo). 2001 Jul;49(7):881-6. doi: 10.1248/cpb.49.881. PMID: 11456096.
9: Matsuo K, Ishida S. Synthesis of murrayaquinone-A. Chem Pharm Bull (Tokyo). 1994 Jun;42(6):1325-7. doi: 10.1248/cpb.42.1325. PMID: 8069978.
10: Itoigawa M, Takeya K, Furukawa H. Structure-activity relationship for the inotropic effect of aromatic methyl-p-quinones. Arch Int Pharmacodyn Ther. 1990 Nov-Dec;308:95-103. PMID: 2099138.
11: 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. PMID: 22480243.
12: Guo J, Kiran IN, Reddy RS, Gao J, Tang M, Liu Y, He Y. Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones. Org Lett. 2016 May 20;18(10):2499-502. doi: 10.1021/acs.orglett.6b01090. Epub 2016 May 5. PMID: 27149368.