BMS-378806
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    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H524472

CAS#: 357263-13-9

Description: BMS-378806 is a small molecule that inhibits the first step of HIV-1 infection by blocking the binding of host cell CD4 with viral gp120 protein. It binds the exterior envelope glycoprotein gp120 (Kd= 21.1 nM; Ki = 24.9 nM), blocking the conformational change that occurs with CD4 binding and preventing fusion of the viral and target cell membranes.


Chemical Structure

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BMS-378806
CAS# 357263-13-9

Theoretical Analysis

Hodoodo Cat#: H524472
Name: BMS-378806
CAS#: 357263-13-9
Chemical Formula: C22H22N4O4
Exact Mass: 406.16
Molecular Weight: 406.430
Elemental Analysis: C, 65.01; H, 5.46; N, 13.78; O, 15.75

Price and Availability

Size Price Availability Quantity
1mg USD 215 2 Weeks
5mg USD 450 2 Weeks
10mg USD 730 2 Weeks
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Synonym: BMS-378806; BMS 378806; BMS378806; BMS-806; BMS806; Bms 806.

IUPAC/Chemical Name: 4-benzoyl-1-((4-methoxy-1H- pyrrolo(2,3-b)pyridin-3-yl)oxoacetyl)-2- (R)-methylpiperazine

InChi Key: FCBQJNCAKZSIAH-NDEPHWFRSA-N

InChi Code: InChI=1S/C21H23FN2O3S/c22-17-3-1-15(2-4-17)13-16-7-9-24(10-8-16)11-12-28(26)18-5-6-19-20(14-18)27-21(25)23-19/h1-6,14,16H,7-13H2,(H,23,25)/t28-/m0/s1

SMILES Code: C[C@@H]1CN(CCN1C(=O)C(=O)c2c[nH]c3c2c(ccn3)OC)C(=O)c4ccccc4

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, not in water

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 406.43 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Patel RV, Park SW. Pyrroloaryls and pyrroloheteroaryls: Inhibitors of the HIV fusion/attachment, reverse transcriptase and integrase. Bioorg Med Chem. 2015 Sep 1;23(17):5247-63. doi: 10.1016/j.bmc.2015.06.016. Epub 2015 Jun 14. Review. PubMed PMID: 26116177.

2: Liu T, Huang B, Zhan P, De Clercq E, Liu X. Discovery of small molecular inhibitors targeting HIV-1 gp120-CD4 interaction drived from BMS-378806. Eur J Med Chem. 2014 Oct 30;86:481-90. doi: 10.1016/j.ejmech.2014.09.012. Epub 2014 Sep 6. Review. PubMed PMID: 25203778.

3: Ölgen S. Recent development of new substituted indole and azaindole derivatives as anti-HIV agents. Mini Rev Med Chem. 2013 Oct;13(12):1700-8. Review. PubMed PMID: 23895189.

4: Sato S, Inokuma T, Otsubo N, Burton DR, Barbas CF 3rd. Chemically Programmed Antibodies AS HIV-1 Attachment Inhibitors. ACS Med Chem Lett. 2013 May 9;4(5):460-465. PubMed PMID: 23750312; PubMed Central PMCID: PMC3673733.

5: Teixeira C, Serradji N, Amroune S, Storck K, Rogez-Kreuz C, Clayette P, Barbault F, Maurel F. Is the conformational flexibility of piperazine derivatives important to inhibit HIV-1 replication? J Mol Graph Model. 2013 Jul;44:91-103. doi: 10.1016/j.jmgm.2013.05.003. Epub 2013 May 13. PubMed PMID: 23748247.

6: Wang T, Yang Z, Zhang Z, Gong YF, Riccardi KA, Lin PF, Parker DD, Rahematpura S, Mathew M, Zheng M, Meanwell NA, Kadow JF, Bender JA. Inhibitors of HIV-1 attachment. Part 10. The discovery and structure-activity relationships of 4-azaindole cores. Bioorg Med Chem Lett. 2013 Jan 1;23(1):213-7. doi: 10.1016/j.bmcl.2012.10.120. Epub 2012 Nov 7. PubMed PMID: 23200254.

7: Li L, Chen H, Zhao RN, Han JG. The investigations on HIV-1 gp120 bound with BMS-488043 by using docking and molecular dynamics simulations. J Mol Model. 2013 Feb;19(2):905-17. doi: 10.1007/s00894-012-1619-5. Epub 2012 Oct 20. PubMed PMID: 23086459.

8: Singh IP, Chauthe SK. Small molecule HIV entry inhibitors: Part II. Attachment and fusion inhibitors: 2004-2010. Expert Opin Ther Pat. 2011 Mar;21(3):399-416. doi: 10.1517/13543776.2011.550876. Review. PubMed PMID: 21342055.

9: Yang Z, Zadjura LM, Marino AM, D'Arienzo CJ, Malinowski J, Gesenberg C, Lin PF, Colonno RJ, Wang T, Kadow JF, Meanwell NA, Hansel SB. Utilization of in vitro Caco-2 permeability and liver microsomal half-life screens in discovering BMS-488043, a novel HIV-1 attachment inhibitor with improved pharmacokinetic properties. J Pharm Sci. 2010 Apr;99(4):2135-52. doi: 10.1002/jps.21948. PubMed PMID: 19780144.

10: Wang T, Yin Z, Zhang Z, Bender JA, Yang Z, Johnson G, Yang Z, Zadjura LM, D'Arienzo CJ, DiGiugno Parker D, Gesenberg C, Yamanaka GA, Gong YF, Ho HT, Fang H, Zhou N, McAuliffe BV, Eggers BJ, Fan L, Nowicka-Sans B, Dicker IB, Gao Q, Colonno RJ, Lin PF, Meanwell NA, Kadow JF. Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 5. An evolution from indole to azaindoles leading to the discovery of 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane -1,2-dione (BMS-488043), a drug candidate that demonstrates antiviral activity in HIV-1-infected subjects. J Med Chem. 2009 Dec 10;52(23):7778-87. doi: 10.1021/jm900843g. PubMed PMID: 19769332.

11: Teixeira C, Serradji N, Maurel F, Barbault F. Docking and 3D-QSAR studies of BMS-806 analogs as HIV-1 gp120 entry inhibitors. Eur J Med Chem. 2009 Sep;44(9):3524-32. doi: 10.1016/j.ejmech.2009.03.028. Epub 2009 Mar 28. PubMed PMID: 19410340.

12: Rossi F, Querido B, Nimmagadda M, Cocklin S, Navas-Martín S, Martín-García J. The V1-V3 region of a brain-derived HIV-1 envelope glycoprotein determines macrophage tropism, low CD4 dependence, increased fusogenicity and altered sensitivity to entry inhibitors. Retrovirology. 2008 Oct 6;5:89. doi: 10.1186/1742-4690-5-89. PubMed PMID: 18837996; PubMed Central PMCID: PMC2576352.

13: Rusconi S, Scozzafava A, Mastrolorenzo A, Supuran CT. An update in the development of HIV entry inhibitors. Curr Top Med Chem. 2007;7(13):1273-89. Review. PubMed PMID: 17627557.

14: Xue YJ, Yan JH, Arnold M, Grasela D, Unger S. Quantitative determination of BMS-378806 in human plasma and urine by high-performance liquid chromatography/tandem mass spectrometry. J Sep Sci. 2007 Jun;30(9):1267-75. PubMed PMID: 17623467.

15: Ketas TJ, Schader SM, Zurita J, Teo E, Polonis V, Lu M, Klasse PJ, Moore JP. Entry inhibitor-based microbicides are active in vitro against HIV-1 isolates from multiple genetic subtypes. Virology. 2007 Aug 1;364(2):431-40. Epub 2007 Apr 10. PubMed PMID: 17428517.

16: Schön A, Madani N, Klein JC, Hubicki A, Ng D, Yang X, Smith AB 3rd, Sodroski J, Freire E. Thermodynamics of binding of a low-molecular-weight CD4 mimetic to HIV-1 gp120. Biochemistry. 2006 Sep 12;45(36):10973-80. PubMed PMID: 16953583; PubMed Central PMCID: PMC2504686.

17: Ho HT, Fan L, Nowicka-Sans B, McAuliffe B, Li CB, Yamanaka G, Zhou N, Fang H, Dicker I, Dalterio R, Gong YF, Wang T, Yin Z, Ueda Y, Matiskella J, Kadow J, Clapham P, Robinson J, Colonno R, Lin PF. Envelope conformational changes induced by human immunodeficiency virus type 1 attachment inhibitors prevent CD4 binding and downstream entry events. J Virol. 2006 Apr;80(8):4017-25. PubMed PMID: 16571818; PubMed Central PMCID: PMC1440438.

18: Koszalka GW, Meanwell NA. Inhibition of virus entry: an antiviral mechanism of emerging prominence. Curr Opin Investig Drugs. 2006 Feb;7(2):106-8. PubMed PMID: 16499279.

19: Kong R, Tan JJ, Ma XH, Chen WZ, Wang CX. Prediction of the binding mode between BMS-378806 and HIV-1 gp120 by docking and molecular dynamics simulation. Biochim Biophys Acta. 2006 Apr;1764(4):766-72. Epub 2006 Jan 18. PubMed PMID: 16455315.

20: Towie N. Drug firms donate compounds for anti-HIV gel. Nature. 2005 Nov 3;438(7064):6-7. PubMed PMID: 16267513.