MedKoo Cat#: 581313 | Name: Dichloroallyl lawsone

Description:

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

Dichloroallyl lawsone (DCL, NSC-126771), a synthetic analogue of the antimalarial lapachol, is potentially useful in cancer chemotherapy.

Chemical Structure

Dichloroallyl lawsone
CAS#36417-16-0

Theoretical Analysis

MedKoo Cat#: 581313

Name: Dichloroallyl lawsone

CAS#: 36417-16-0

Chemical Formula: C13H8Cl2O3

Exact Mass: 281.9850

Molecular Weight: 283.10

Elemental Analysis: C, 55.15; H, 2.85; Cl, 25.04; O, 16.95

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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Synonym
Dichloroallyl lawsone; Dichloroallyllawsone; Dichlorolapachol; Dichlorolawsone;
IUPAC/Chemical Name
1,4-Naphthoquinone, 2-(3,3-dichloroallyl)-3-hydroxy-
InChi Key
LKEVYYRGUCTKBS-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H8Cl2O3/c14-10(15)6-5-9-11(16)7-3-1-2-4-8(7)12(17)13(9)18/h1-4,6,18H,5H2
SMILES Code
O=C(C1=C2C=CC=C1)C(O)=C(C/C=C(Cl)\Cl)C2=O
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 283.10 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: Peters GJ. Antipyrimidine effects of five different pyrimidine de novo synthesis inhibitors in three head and neck cancer cell lines. Nucleosides Nucleotides Nucleic Acids. 2018;37(6):329-339. doi: 10.1080/15257770.2018.1460479. Epub 2018 May 3. PubMed PMID: 29723133. 2: Al-Sanea MM, Elkamhawy A, Zakaria A, Park BS, Kwon Y, Lee SH, Lee SW, Kim IT. Synthesis and in vitro screening of phenylbipyridinylpyrazole derivatives as potential antiproliferative agents. Molecules. 2015 Jan 9;20(1):1031-45. doi: 10.3390/molecules20011031. PubMed PMID: 25584833. 3: Jali BR, Kuang Y, Neamati N, Baruah JB. Selective binding of naphthoquinone derivatives to serum albumin proteins and their effects on cytotoxicity. Chem Biol Interact. 2014 May 5;214:10-7. doi: 10.1016/j.cbi.2014.01.014. Epub 2014 Feb 18. PubMed PMID: 24560625. 4: Pradhan R, Dandawate P, Vyas A, Padhye S, Biersack B, Schobert R, Ahmad A, Sarkar FH. From body art to anticancer activities: perspectives on medicinal properties of henna. Curr Drug Targets. 2012 Dec;13(14):1777-98. Review. PubMed PMID: 23140289. 5: Löffler M, Knecht W, Rawls J, Ullrich A, Dietz C. Drosophila melanogaster dihydroorotate dehydrogenase: the N-terminus is important for biological function in vivo but not for catalytic properties in vitro. Insect Biochem Mol Biol. 2002 Sep;32(9):1159-69. PubMed PMID: 12213251. 6: Baldwin J, Farajallah AM, Malmquist NA, Rathod PK, Phillips MA. Malarial dihydroorotate dehydrogenase. Substrate and inhibitor specificity. J Biol Chem. 2002 Nov 1;277(44):41827-34. Epub 2002 Aug 19. PubMed PMID: 12189151. 7: Knecht W, Löffler M. Redoxal as a new lead structure for dihydroorotate dehydrogenase inhibitors: a kinetic study of the inhibition mechanism. FEBS Lett. 2000 Feb 4;467(1):27-30. PubMed PMID: 10664450. 8: Cleaveland ES, Monks A, Vaigro-Wolff A, Zaharevitz DW, Paull K, Ardalan K, Cooney DA, Ford H Jr. Site of action of two novel pyrimidine biosynthesis inhibitors accurately predicted by the compare program. Biochem Pharmacol. 1995 Mar 30;49(7):947-54. PubMed PMID: 7741767. 9: Chen SF, Perrella FW, Behrens DL, Papp LM. Inhibition of dihydroorotate dehydrogenase activity by brequinar sodium. Cancer Res. 1992 Jul 1;52(13):3521-7. PubMed PMID: 1617622. 10: Boothman DA, Trask DK, Pardee AB. Inhibition of potentially lethal DNA damage repair in human tumor cells by beta-lapachone, an activator of topoisomerase I. Cancer Res. 1989 Feb 1;49(3):605-12. PubMed PMID: 2535961. 11: Kemp AJ, Lyons SD, Christopherson RI. Effects of acivicin and dichloroallyl lawsone upon pyrimidine biosynthesis in mouse L1210 leukemia cells. J Biol Chem. 1986 Nov 15;261(32):14891-5. PubMed PMID: 3771555. 12: Otten SL, Rosazza JP. Oxidative ring fission of the naphthoquinones lapachol and dichloroallyl lawsone by Penicillium notatum. J Biol Chem. 1983 Feb 10;258(3):1610-3. PubMed PMID: 6822525. 13: McKelvey EM, Lomedico M, Lu K, Chadwick M, Loo TL. Dichloroallyl lawsone. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):586-90. PubMed PMID: 436360. 14: Loo TL, Benjamin RS, Lu K, Benvenuto JA, Hall SW, McKelvey EM. Metabolism and disposition of Baker's antifolate (NSC-139105), ftorafur (NSC-148958), and dichloroallyl lawsone (NSC-126771) in man. Drug Metab Rev. 1978;8(1):137-50. PubMed PMID: 363378.