BMS 378806

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

MedKoo CAT#: 584233

CAS#: 357263-14-0

Description: BMS-378806 is an orally bioavailable HIV-1 inhibitor that interferes with gp120-CD4 interaction.

Chemical Structure

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BMS 378806
CAS# 357263-14-0
Instruction

Theoretical Analysis

MedKoo Cat#: 584233
Name: BMS 378806
CAS#: 357263-14-0
Chemical Formula: C22H22N4O4
Exact Mass: 406.16
Molecular Weight: 406.442
Elemental Analysis: C, 65.01; H, 5.46; N, 13.78; O, 15.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: BMS 378806; BMS-378806; BMS378806

IUPAC/Chemical Name: Piperazine, 4-benzoyl-1-(2-(4-methoxy-1H-pyrrolo(2,3-b)pyridin-3-yl)-1,2-dioxoethyl)-2-methyl-, (2S)-

InChi Key: OKGPFTLYBPQBIX-AWEZNQCLSA-N

InChi Code: InChI=1S/C22H22N4O4/c1-14-13-25(21(28)15-6-4-3-5-7-15)10-11-26(14)22(29)19(27)16-12-24-20-18(16)17(30-2)8-9-23-20/h3-9,12,14H,10-11,13H2,1-2H3,(H,23,24)/t14-/m0/s1

SMILES Code: C[C@@H]1N(C(C(C2=CNC3=NC=CC(OC)=C32)=O)=O)CCN(C(C4=CC=CC=C4)=O)C1

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 406.44 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: 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.

2: Moore PL, Cilliers T, Morris L. Predicted genotypic resistance to the novel entry inhibitor, BMS-378806, among HIV-1 isolates of subtypes A to G. AIDS. 2004 Nov 19;18(17):2327-30. PubMed PMID: 15577547.

3: 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.

4: Wang T, Zhang Z, Wallace OB, Deshpande M, Fang H, Yang Z, Zadjura LM, Tweedie DL, Huang S, Zhao F, Ranadive S, Robinson BS, Gong YF, Ricarrdi K, Spicer TP, Deminie C, Rose R, Wang HG, Blair WS, Shi PY, Lin PF, Colonno RJ, Meanwell NA. Discovery of 4-benzoyl-1-[(4-methoxy-1H- pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2- (R)-methylpiperazine (BMS-378806): a novel HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions. J Med Chem. 2003 Sep 25;46(20):4236-9. PubMed PMID: 13678401.

5: 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.

6: 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.

7: 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.

8: 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.

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 HG, Williams RE, Lin PF. A novel class of HIV-1 inhibitors that targets the viral envelope and inhibits CD4 receptor binding. Curr Pharm Des. 2004;10(15):1785-93. Review. PubMed PMID: 15180540.

11: Lin PF, Blair W, Wang T, Spicer T, Guo Q, Zhou N, Gong YF, Wang HG, Rose R, Yamanaka G, Robinson B, Li CB, Fridell R, Deminie C, Demers G, Yang Z, Zadjura L, Meanwell N, Colonno R. A small molecule HIV-1 inhibitor that targets the HIV-1 envelope and inhibits CD4 receptor binding. Proc Natl Acad Sci U S A. 2003 Sep 16;100(19):11013-8. Epub 2003 Aug 20. PubMed PMID: 12930892; PubMed Central PMCID: PMC196918.

12: 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.

13: 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.

14: Veazey RS, Klasse PJ, Schader SM, Hu Q, Ketas TJ, Lu M, Marx PA, Dufour J, Colonno RJ, Shattock RJ, Springer MS, Moore JP. Protection of macaques from vaginal SHIV challenge by vaginally delivered inhibitors of virus-cell fusion. Nature. 2005 Nov 3;438(7064):99-102. Epub 2005 Oct 30. PubMed PMID: 16258536.

15: 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.

16: 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.

17: 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.

18: 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.

19: Madani N, Perdigoto AL, Srinivasan K, Cox JM, Chruma JJ, LaLonde J, Head M, Smith AB 3rd, Sodroski JG. Localized changes in the gp120 envelope glycoprotein confer resistance to human immunodeficiency virus entry inhibitors BMS-806 and #155. J Virol. 2004 Apr;78(7):3742-52. PubMed PMID: 15016894; PubMed Central PMCID: PMC371073.

20: 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.