A-419259 | CAS#364042-47-7 | Src inhibitor

A-419259
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555204

CAS#: 364042-47-7 (free base)

Description: A-419259 is a potent inhibitor of Src family kinases. IC50 values for src, lck, blk, csk, fyn and lyn range between 15 and 50 nM.

Chemical Structure

A-419259

CAS# 364042-47-7 (free base)

Instruction

Theoretical Analysis

MedKoo Cat#: 555204
Name: A-419259
CAS#: 364042-47-7 (free base)
Chemical Formula: C29H34N6O
Exact Mass: 482.28
Molecular Weight: 482.632
Elemental Analysis: C, 72.17; H, 7.10; N, 17.41; O, 3.31

Price and Availability

Size	Price	Availability
5mg	USD 450	2 Weeks
10mg	USD 750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 364042-47-7 (free base)

Synonym: A-419259; A419259; A 419259; RK20449; RK-20449; RK 20449

IUPAC/Chemical Name: 7-[Trans-4-(4-methyl-1-piperazinyl)cyclohexyl]-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

InChi Key: FDVSOQRNTAPCHB-YHBQERECSA-N

InChi Code: InChI=1S/C29H34N6O/c1-33-15-17-34(18-16-33)22-9-11-23(12-10-22)35-19-26(27-28(30)31-20-32-29(27)35)21-7-13-25(14-8-21)36-24-5-3-2-4-6-24/h2-8,13-14,19-20,22-23H,9-12,15-18H2,1H3,(H2,30,31,32)/t22-,23-

SMILES Code: NC1=C2C(N([C@H]3CC[C@H](N4CCN(C)CC4)CC3)C=C2C5=CC=C(OC6=CC=CC=C6)C=C5)=NC=N1

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Soluble in DMSO	0.0	100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 482.63 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Patel RK, Patel YK, Smithgall TE. In Vitro Evolution Reveals a Single Mutation as Sole Source of Src-Family Kinase C-Helix-out Inhibitor Resistance. ACS Chem Biol. 2020 Aug 21;15(8):2175-2184. doi: 10.1021/acschembio.0c00373. Epub 2020 Jul 15. PMID: 32602694; PMCID: PMC8136437.

2: Pene-Dumitrescu T, Peterson LF, Donato NJ, Smithgall TE. An inhibitor- resistant mutant of Hck protects CML cells against the antiproliferative and apoptotic effects of the broad-spectrum Src family kinase inhibitor A-419259. Oncogene. 2008 Nov 27;27(56):7055-69. doi: 10.1038/onc.2008.330. Epub 2008 Sep 15. PMID: 18794796; PMCID: PMC2738638.

3: Du S, Alvarado JJ, Wales TE, Moroco JA, Engen JR, Smithgall TE. ATP-site inhibitors induce unique conformations of the acute myeloid leukemia-associated Src-family kinase, Fgr. Structure. 2022 Nov 3;30(11):1508-1517.e3. doi: 10.1016/j.str.2022.08.008. Epub 2022 Sep 16. PMID: 36115344; PMCID: PMC9637690.

4: Kim Y, Hayashi M, Ono T, Yoda T, Takayanagi H, Nakashima T. Suppression of hematopoietic cell kinase ameliorates the bone destruction associated with inflammation. Mod Rheumatol. 2020 Jan;30(1):85-92. doi: 10.1080/14397595.2018.1553266. Epub 2019 Jan 8. PMID: 30486712.

5: Zhang X, Meyn MA 3rd, Smithgall TE. c-Yes tyrosine kinase is a potent suppressor of ES cell differentiation and antagonizes the actions of its closest phylogenetic relative, c-Src. ACS Chem Biol. 2014 Jan 17;9(1):139-46. doi: 10.1021/cb400249b. Epub 2013 Aug 15. PMID: 23895624; PMCID: PMC3875617.

6: Patel RK, Weir MC, Shen K, Snyder D, Cooper VS, Smithgall TE. Expression of myeloid Src-family kinases is associated with poor prognosis in AML and influences Flt3-ITD kinase inhibitor acquired resistance. PLoS One. 2019 Dec 2;14(12):e0225887. doi: 10.1371/journal.pone.0225887. PMID: 31790499; PMCID: PMC6886798.

7: Parker LJ, Taruya S, Tsuganezawa K, Ogawa N, Mikuni J, Honda K, Tomabechi Y, Handa N, Shirouzu M, Yokoyama S, Tanaka A. Kinase crystal identification and ATP-competitive inhibitor screening using the fluorescent ligand SKF86002. Acta Crystallogr D Biol Crystallogr. 2014 Feb;70(Pt 2):392-404. doi: 10.1107/S1399004713028654. Epub 2014 Jan 29. PMID: 24531473.

8: Wilson MB, Schreiner SJ, Choi HJ, Kamens J, Smithgall TE. Selective pyrrolo- pyrimidine inhibitors reveal a necessary role for Src family kinases in Bcr-Abl signal transduction and oncogenesis. Oncogene. 2002 Nov 21;21(53):8075-88. doi: 10.1038/sj.onc.1206008. PMID: 12444544.

9: Zhang X, Simerly C, Hartnett C, Schatten G, Smithgall TE. Src-family tyrosine kinase activities are essential for differentiation of human embryonic stem cells. Stem Cell Res. 2014 Nov;13(3 Pt A):379-89. doi: 10.1016/j.scr.2014.09.007. Epub 2014 Sep 30. PMID: 25305536; PMCID: PMC4252886.

10: Quatredeniers M, Nakhleh MK, Dumas SJ, Courboulin A, Vinhas MC, Antigny F, Phan C, Guignabert C, Bendifallah I, Vocelle M, Fadel E, Dorfmüller P, Humbert M, Cohen-Kaminsky S. Functional interaction between PDGFβ and GluN2B-containing NMDA receptors in smooth muscle cell proliferation and migration in pulmonary arterial hypertension. Am J Physiol Lung Cell Mol Physiol. 2019 Mar 1;316(3):L445-L455. doi: 10.1152/ajplung.00537.2017. Epub 2018 Dec 13. PMID: 30543306.

11: Dincer S, Cetin KT, Onay-Besikci A, Ölgen S. Synthesis, biological evaluation and docking studies of new pyrrolo[2,3-d] pyrimidine derivatives as Src family-selective tyrosine kinase inhibitors. J Enzyme Inhib Med Chem. 2013 Oct;28(5):1080-7. doi: 10.3109/14756366.2012.715288. Epub 2012 Sep 7. PMID: 22957720.

12: Zhang Q, Thomas SM, Xi S, Smithgall TE, Siegfried JM, Kamens J, Gooding WE, Grandis JR. SRC family kinases mediate epidermal growth factor receptor ligand cleavage, proliferation, and invasion of head and neck cancer cells. Cancer Res. 2004 Sep 1;64(17):6166-73. doi: 10.1158/0008-5472.CAN-04-0504. PMID: 15342401.

13: Meyn MA 3rd, Schreiner SJ, Dumitrescu TP, Nau GJ, Smithgall TE. SRC family kinase activity is required for murine embryonic stem cell growth and differentiation. Mol Pharmacol. 2005 Nov;68(5):1320-30. doi: 10.1124/mol.104.010231. Epub 2005 Jun 28. PMID: 15985613.

14: Je DW, O YM, Ji YG, Cho Y, Lee DH. The inhibition of SRC family kinase suppresses pancreatic cancer cell proliferation, migration, and invasion. Pancreas. 2014 Jul;43(5):768-76. doi: 10.1097/MPA.0000000000000103. PMID: 24763074.

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