NBD-556
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MedKoo CAT#: 526801

CAS#: 333353-44-9

Description: NBD-556 is a HIV-1 entry inhibitor. NBD-556 inhibited cell–cell fusion between H9/HIV-1IIIB and MT-2 (IC50 ~3 μM). NBD-556 prevent gp120 binding to CD4. The HIV-1 entry into host cells is a complex, multi-factors involved, and multi-step process. Especially, the attachment of HIV-1 envelope glycoprotein gp120 to the host cell receptor CD4 is the first key step during entry process, representing a promising antiviral therapeutic target.


Price and Availability

Size Price Shipping out time Quantity
25mg USD 410 2 Weeks
100mg USD 1000 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-08-03. Prices are subject to change without notice.

NBD-556, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526801
Name: NBD-556
CAS#: 333353-44-9
Chemical Formula: C17H24ClN3O2
Exact Mass: 337.1557
Molecular Weight: 337.848
Elemental Analysis: C, 60.44; H, 7.16; Cl, 10.49; N, 12.44; O, 9.47


Synonym: NBD-556; NBD 556; NBD556.

IUPAC/Chemical Name: N1-(4-chlorophenyl)-N2-(2,2,6,6-tetramethylpiperidin-4-yl)oxalamide

InChi Key: ZKXLQCIOURANAD-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H24ClN3O2/c1-16(2)9-13(10-17(3,4)21-16)20-15(23)14(22)19-12-7-5-11(18)6-8-12/h5-8,13,21H,9-10H2,1-4H3,(H,19,22)(H,20,23)

SMILES Code: O=C(NC1CC(C)(C)NC(C)(C)C1)C(NC2=CC=C(Cl)C=C2)=O


Technical Data

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


References

1: Curreli F, Kwon YD, Zhang H, Scacalossi D, Belov DS, Tikhonov AA, Andreev IA, Altieri A, Kurkin AV, Kwong PD, Debnath AK. Structure-Based Design of a Small Molecule CD4-Antagonist with Broad Spectrum Anti-HIV-1 Activity. J Med Chem. 2015 Sep 10;58(17):6909-27. doi: 10.1021/acs.jmedchem.5b00709. Epub 2015 Aug 28. PubMed PMID: 26301736; PubMed Central PMCID: PMC4676410.

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: Curreli F, Kwon YD, Zhang H, Yang Y, Scacalossi D, Kwong PD, Debnath AK. Binding mode characterization of NBD series CD4-mimetic HIV-1 entry inhibitors by X-ray structure and resistance study. Antimicrob Agents Chemother. 2014 Sep;58(9):5478-91. doi: 10.1128/AAC.03339-14. Epub 2014 Jul 7. PubMed PMID: 25001301; PubMed Central PMCID: PMC4135886.

4: Guttman M, Garcia NK, Cupo A, Matsui T, Julien JP, Sanders RW, Wilson IA, Moore JP, Lee KK. CD4-induced activation in a soluble HIV-1 Env trimer. Structure. 2014 Jul 8;22(7):974-84. doi: 10.1016/j.str.2014.05.001. Epub 2014 Jun 12. PubMed PMID: 24931470; PubMed Central PMCID: PMC4231881.

5: Kwon YD, LaLonde JM, Yang Y, Elban MA, Sugawara A, Courter JR, Jones DM, Smith AB 3rd, Debnath AK, Kwong PD. Crystal structures of HIV-1 gp120 envelope glycoprotein in complex with NBD analogues that target the CD4-binding site. PLoS One. 2014 Jan 28;9(1):e85940. doi: 10.1371/journal.pone.0085940. eCollection 2014. PubMed PMID: 24489681; PubMed Central PMCID: PMC3904841.

6: Schön A, Brown RK, Hutchins BM, Freire E. Ligand binding analysis and screening by chemical denaturation shift. Anal Biochem. 2013 Dec 1;443(1):52-7. doi: 10.1016/j.ab.2013.08.015. Epub 2013 Aug 29. PubMed PMID: 23994566; PubMed Central PMCID: PMC3809086.

7: LaLonde JM, Kwon YD, Jones DM, Sun AW, Courter JR, Soeta T, Kobayashi T, Princiotto AM, Wu X, Schön A, Freire E, Kwong PD, Mascola JR, Sodroski J, Madani N, Smith AB 3rd. Structure-based design, synthesis, and characterization of dual hotspot small-molecule HIV-1 entry inhibitors. J Med Chem. 2012 May 10;55(9):4382-96. doi: 10.1021/jm300265j. Epub 2012 Apr 23. PubMed PMID: 22497421; PubMed Central PMCID: PMC3376652.

8: Kwon YD, Finzi A, Wu X, Dogo-Isonagie C, Lee LK, Moore LR, Schmidt SD, Stuckey J, Yang Y, Zhou T, Zhu J, Vicic DA, Debnath AK, Shapiro L, Bewley CA, Mascola JR, Sodroski JG, Kwong PD. Unliganded HIV-1 gp120 core structures assume the CD4-bound conformation with regulation by quaternary interactions and variable loops. Proc Natl Acad Sci U S A. 2012 Apr 10;109(15):5663-8. doi: 10.1073/pnas.1112391109. Epub 2012 Mar 26. PubMed PMID: 22451932; PubMed Central PMCID: PMC3326499.

9: Dogo-Isonagie C, Lam S, Gustchina E, Acharya P, Yang Y, Shahzad-ul-Hussan S, Clore GM, Kwong PD, Bewley CA. Peptides from second extracellular loop of C-C chemokine receptor type 5 (CCR5) inhibit diverse strains of HIV-1. J Biol Chem. 2012 Apr 27;287(18):15076-86. doi: 10.1074/jbc.M111.332361. Epub 2012 Mar 8. PubMed PMID: 22403408; PubMed Central PMCID: PMC3340262.

10: Shrivastava I, LaLonde JM. Enhanced dynamics of HIV gp120 glycoprotein by small molecule binding. Biochemistry. 2011 May 17;50(19):4173-83. doi: 10.1021/bi2002218. Epub 2011 Apr 21. PubMed PMID: 21488663; PubMed Central PMCID: PMC3121314.

11: 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.

12: Schön A, Madani N, Smith AB, Lalonde JM, Freire E. Some binding-related drug properties are dependent on thermodynamic signature. Chem Biol Drug Des. 2011 Mar;77(3):161-5. doi: 10.1111/j.1747-0285.2010.01075.x. Epub 2011 Feb 2. PubMed PMID: 21288305; PubMed Central PMCID: PMC3079564.

13: Yoshimura K, Harada S, Shibata J, Hatada M, Yamada Y, Ochiai C, Tamamura H, Matsushita S. Enhanced exposure of human immunodeficiency virus type 1 primary isolate neutralization epitopes through binding of CD4 mimetic compounds. J Virol. 2010 Aug;84(15):7558-68. doi: 10.1128/JVI.00227-10. Epub 2010 May 26. PubMed PMID: 20504942; PubMed Central PMCID: PMC2897603.

14: Brower ET, Schön A, Freire E. Naturally occurring variability in the envelope glycoprotein of HIV-1 and development of cell entry inhibitors. Biochemistry. 2010 Mar 23;49(11):2359-67. doi: 10.1021/bi1000933. PubMed PMID: 20166763; PubMed Central PMCID: PMC2840190.

15: Madani N, Schön A, Princiotto AM, Lalonde JM, Courter JR, Soeta T, Ng D, Wang L, Brower ET, Xiang SH, Kwon YD, Huang CC, Wyatt R, Kwong PD, Freire E, Smith AB 3rd, Sodroski J. Small-molecule CD4 mimics interact with a highly conserved pocket on HIV-1 gp120. Structure. 2008 Nov 12;16(11):1689-701. doi: 10.1016/j.str.2008.09.005. PubMed PMID: 19000821; PubMed Central PMCID: PMC2597202.

16: Repik A, Clapham PR. Plugging gp120s cavity. Structure. 2008 Nov 12;16(11):1603-4. doi: 10.1016/j.str.2008.10.003. PubMed PMID: 19000812.

17: 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.

18: Zhao Q, Ma L, Jiang S, Lu H, Liu S, He Y, Strick N, Neamati N, Debnath AK. Identification of N-phenyl-N'-(2,2,6,6-tetramethyl-piperidin-4-yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4. Virology. 2005 Sep 1;339(2):213-25. PubMed PMID: 15996703.