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MedKoo Cat#: 527504 | Name: BMS-433771 free base

Description:

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

BMS-433771 is a novel inhibitor of respiratory syncytial virus (RSV), binding the RSV F glycoprotein and inhibiting membrane fusion.

Chemical Structure

BMS-433771 free base
BMS-433771 free base
CAS#543700-68-1 (free base)

Theoretical Analysis

MedKoo Cat#: 527504

Name: BMS-433771 free base

CAS#: 543700-68-1 (free base)

Chemical Formula: C21H23N5O2

Exact Mass: 377.1852

Molecular Weight: 377.45

Elemental Analysis: C, 66.83; H, 6.14; N, 18.55; O, 8.48

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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Related CAS #
380603-12-3 (HCl) 543700-68-1 (free base) 543700-67-0 (HCl hydrate)
Synonym
BMS433771; BMS 433771; BMS-433771
IUPAC/Chemical Name
1-Cyclopropyl-3-[[1-(4-hydroxybutyl)benzimidazol-2-yl]methyl]imidazo[4,5-c]pyridin-2-one
InChi Key
KSHJXDWYTZJUEI-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H23N5O2/c27-12-4-3-11-24-17-6-2-1-5-16(17)23-20(24)14-25-19-13-22-10-9-18(19)26(21(25)28)15-7-8-15/h1-2,5-6,9-10,13,15,27H,3-4,7-8,11-12,14H2
SMILES Code
O=C(N1C2CC2)N(CC3=NC4=CC=CC=C4N3CCCCO)C5=C1C=CN=C5
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

Preparing Stock Solutions

The following data is based on the product molecular weight 377.45 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: Haid S, Grethe C, Bankwitz D, Grunwald T, Pietschmann T. Identification of a Human Respiratory Syncytial Virus Cell Entry Inhibitor by Using a Novel Lentiviral Pseudotype System. J Virol. 2015 Dec 30;90(6):3065-73. doi: 10.1128/JVI.03074-15. PubMed PMID: 26719246; PubMed Central PMCID: PMC4810627. 2: Ji D, Ye W, Chen H. Revealing the binding mode between respiratory syncytial virus fusion protein and benzimidazole-based inhibitors. Mol Biosyst. 2015 Jul;11(7):1857-66. doi: 10.1039/c5mb00036j. PubMed PMID: 25872614. 3: Magro M, Andreu D, Gómez-Puertas P, Melero JA, Palomo C. Neutralization of human respiratory syncytial virus infectivity by antibodies and low-molecular-weight compounds targeted against the fusion glycoprotein. J Virol. 2010 Aug;84(16):7970-82. doi: 10.1128/JVI.00447-10. Epub 2010 Jun 9. PubMed PMID: 20534864; PubMed Central PMCID: PMC2916552. 4: Sin N, Venables BL, Combrink KD, Gulgeze HB, Yu KL, Civiello RL, Thuring J, Wang XA, Yang Z, Zadjura L, Marino A, Kadow KF, Cianci CW, Clarke J, Genovesi EV, Medina I, Lamb L, Krystal M, Meanwell NA. Respiratory syncytial virus fusion inhibitors. Part 7: structure-activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4857-62. doi: 10.1016/j.bmcl.2009.06.030. Epub 2009 Jun 13. PubMed PMID: 19596574. 5: Del Vecchio AM, Sarisky RT. Cold virus fusion or stopping fusion cold--inhibitors of the human respiratory syncytial virus F protein. Recent Pat Antiinfect Drug Discov. 2006 Jun;1(2):247-54. Review. PubMed PMID: 18221150. 6: Combrink KD, Gulgeze HB, Thuring JW, Yu KL, Civiello RL, Zhang Y, Pearce BC, Yin Z, Langley DR, Kadow KF, Cianci CW, Li Z, Clarke J, Genovesi EV, Medina I, Lamb L, Yang Z, Zadjura L, Krystal M, Meanwell NA. Respiratory syncytial virus fusion inhibitors. Part 6: an examination of the effect of structural variation of the benzimidazol-2-one heterocycle moiety. Bioorg Med Chem Lett. 2007 Sep 1;17(17):4784-90. Epub 2007 Jun 26. PubMed PMID: 17616396. 7: Wang XA, Cianci CW, Yu KL, Combrink KD, Thuring JW, Zhang Y, Civiello RL, Kadow KF, Roach J, Li Z, Langley DR, Krystal M, Meanwell NA. Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity. Bioorg Med Chem Lett. 2007 Aug 15;17(16):4592-8. Epub 2007 Jun 8. PubMed PMID: 17576060. 8: Yu KL, Sin N, Civiello RL, Wang XA, Combrink KD, Gulgeze HB, Venables BL, Wright JJ, Dalterio RA, Zadjura L, Marino A, Dando S, D'Arienzo C, Kadow KF, Cianci CW, Li Z, Clarke J, Genovesi EV, Medina I, Lamb L, Colonno RJ, Yang Z, Krystal M, Meanwell NA. Respiratory syncytial virus fusion inhibitors. Part 4: optimization for oral bioavailability. Bioorg Med Chem Lett. 2007 Feb 15;17(4):895-901. Epub 2006 Dec 1. Erratum in: Bioorg Med Chem Lett. 2007 Apr 15;17(8):2385. PubMed PMID: 17169560. 9: Debnath AK. Prospects and strategies for the discovery and development of small-molecule inhibitors of six-helix bundle formation in class 1 viral fusion proteins. Curr Opin Investig Drugs. 2006 Feb;7(2):118-27. Review. Erratum in: Curr Opin Investig Drugs. 2006 Apr;7(4):389. PubMed PMID: 16499281. 10: Holzgrabe U, Bennack E. [An orally available viral fusion inhibitor found]. Pharm Unserer Zeit. 2005;34(3):182-3. German. PubMed PMID: 15942992. 11: Gao GF. Filling the hole: evidence of a small molecule binding to the fusion core pocket in human respiratory syncytial virus. Expert Opin Investig Drugs. 2005 Feb;14(2):195-7. Review. PubMed PMID: 15757395. 12: Cianci C, Meanwell N, Krystal M. Antiviral activity and molecular mechanism of an orally active respiratory syncytial virus fusion inhibitor. J Antimicrob Chemother. 2005 Mar;55(3):289-92. Epub 2005 Jan 28. Review. PubMed PMID: 15681582. 13: Cianci C, Langley DR, Dischino DD, Sun Y, Yu KL, Stanley A, Roach J, Li Z, Dalterio R, Colonno R, Meanwell NA, Krystal M. Targeting a binding pocket within the trimer-of-hairpins: small-molecule inhibition of viral fusion. Proc Natl Acad Sci U S A. 2004 Oct 19;101(42):15046-51. Epub 2004 Oct 6. PubMed PMID: 15469910; PubMed Central PMCID: PMC523459. 14: Cianci C, Genovesi EV, Lamb L, Medina I, Yang Z, Zadjura L, Yang H, D'Arienzo C, Sin N, Yu KL, Combrink K, Li Z, Colonno R, Meanwell N, Clark J, Krystal M. Oral efficacy of a respiratory syncytial virus inhibitor in rodent models of infection. Antimicrob Agents Chemother. 2004 Jul;48(7):2448-54. PubMed PMID: 15215093; PubMed Central PMCID: PMC434195. 15: Cianci C, Yu KL, Combrink K, Sin N, Pearce B, Wang A, Civiello R, Voss S, Luo G, Kadow K, Genovesi EV, Venables B, Gulgeze H, Trehan A, James J, Lamb L, Medina I, Roach J, Yang Z, Zadjura L, Colonno R, Clark J, Meanwell N, Krystal M. Orally active fusion inhibitor of respiratory syncytial virus. Antimicrob Agents Chemother. 2004 Feb;48(2):413-22. PubMed PMID: 14742189; PubMed Central PMCID: PMC321540.