L-689502

Names

[ CAS No. ]:
138483-63-3

[ Name ]:
L-689502

[Synonym ]:
Des-3-pyridylmethyl Indinavir
(2S)-1-[(2S,4S)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl]-N-tert-butylpiperazine-2-carboxamide
[14C]-N-Dealkyl Indinavir
N-(2(R)-hydroxy-1(S)-indanyl)-2(R)-phenylmethyl-4(S)-hydroxy-5-(1-(2(S)-N-(tert-butylcarboxamido)piperazinyl))pentanamide
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2(R)-({4-[2-(4-morpholinyl)ethoxy]phenyl}methyl)hexanamide
(1S,2R,2'R,4'S,2"S)-1-((2-benzyl-5-(((2-(t-butyl)amino)carbonyl)piperazin-1-yl)-4-hydroxypentanoyl)amino)indan-2-ol
indinavir penultimate
2,3,5-Trideoxy-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]-5-[(2S)-2-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperazinyl]-2-(phenylmethyl)-D-erythro-pentonamide
N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-(1,1-dimethylethoxycarbonyl)amino-4(S)-hydroxy-6-phenyl-2(R)-(4-(2-(4-morpholinyl)ethoxy)phenyl)methyl hexanamide
L-689502

Biological Activity

[Description]:

L-689502 is a potent inhibitor of HIV-l protease with an IC50 of 1 nM.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> HIV Protease
Research Areas >> Inflammation/Immunology

[Target]

IC50: 1 nM (HIV-l protease)[1]


[In Vitro]

Both L694746 and L-689502 inhibit HIV-l ptotease activity in a concentration-dependent manner. Pepstatin is much less potent than either compound exhibiting an IC50 of 2 μM. L694746 is as potent as L-689502 in inhibiting the HIV-l protease despite being structurally different from L-689502[1].

[Cell Assay]

G689502 (3.3 pmoles in 1 mL of 100% DMSO) is added to cultures that have been growing for 48 hr. The final substrate and DMSO concentrations during the fermentation period are 65 pM and 2%, respectively. The fermentations containing L-689502 are carried out for an additional 72-96 hr prior to be harvested.The whole broth is sequenthdly extracted with methanol (0.5 vol) and acetone (0.5 vol). The supematant containing the derivatives of L-689502 is separated from the mycelia by filtration[1].

[References]

[1]. Lingham RB, et al. HIV-1 protease inhibitory activity of L-694,746, a novel metabolite of L-689,502. Biochem Biophys Res Commun. 1991 Dec 31;181(3):1456-61.


[Related Small Molecules]

Pepstatin | Tipranavir | Nelfinavir mesylate | Lopinavir | Indinavir Sulfate | DPC-681 | PNU-103017

Chemical & Physical Properties

[ Density]:
1.24g/cm3

[ Boiling Point ]:
886.9ºC at 760 mmHg

[ Molecular Formula ]:
C39H51N3O7

[ Molecular Weight ]:
673.83800

[ Flash Point ]:
490.2ºC

[ Exact Mass ]:
673.37300

[ PSA ]:
136.57000

[ LogP ]:
5.20040

[ Vapour Pressure ]:
9.83E-34mmHg at 25°C

[ Index of Refraction ]:
1.615

[ Storage condition ]:
2-8℃

Synthetic Route

Precursor & DownStream


Related Compounds