150840-28-1

Basic information

• Product Name: 7-{[(3beta)-3-hydroxy-28-oxolup-20(29)-en-28-yl]amino}heptanoic acid
• CAS NO: 150840-28-1
• Molecular Formula: C₃₇H₆₁NO₄
• Molecular Weight: 583.8845
• Mol File: 150840-28-1.mol

Chemical Properties

• Boiling Point: 704.8°C at 760 mmHg
• Flash Point: 380°C
• Density: 1.061g/cm³
• Vapor Pressure: 5.86E-23mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 7-{[(3beta)-3-hydroxy-28-oxolup-20(29)-en-28-yl]amino}heptanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-{[(3beta)-3-hydroxy-28-oxolup-20(29)-en-28-yl]amino}heptanoic acid(150840-28-1)
• EPA Substance Registry System: 7-{[(3beta)-3-hydroxy-28-oxolup-20(29)-en-28-yl]amino}heptanoic acid(150840-28-1)

Safety Data

• Hazardous Substances Data: 150840-28-1(Hazardous Substances Data)

Upstream product

• 17994-94-4 methyl 7-aminoheptanoate hydrochloride 
• 59868-82-5 3-O-acetylbetulinic acid chloride 
• 1169880-18-5 C₄₆H₆₉NO₅ 
• 10376-50-8 3-O-acetylbetulinic acid 

Relevant articles and documents

New betulinic acid derivatives for bevirimat-resistant human immunodeficiency virus type-1

Bevirimat (1, BVM) is an anti-HIV agent that blocks HIV-1 replication by interfering with HIV-1 Gag-SP1 processing at a late stage of viral maturation. However, clinical trials of 1 have revealed a high baseline drug resistance that is attributed to naturally occurring polymorphisms in HIV-1 Gag. To overcome the drug resistance, 28 new derivatives of 1 were synthesized and tested against compound 1-resistant (BVM-R) HIV-1 variants. Among them, compound 6 exhibited much improved activity against several HIV-1 strains carrying BVM-R polymorphisms. Compound 6 was at least 20-fold more potent than 1 against the replication of NL4-3/V370A, which carries the most prevalent clinical BVM-R polymorphism in HIV-1 Gag-SP1. Thus, compound 6 merits further development as a potential anti-AIDS clinical trial candidate.

Synthesis of betulinic acid derivatives as entry inhibitors against HIV-1 and bevirimat-resistant HIV-1 variants

Betulinic acid derivatives modified at the C28 position are HIV-1entry inhibitors such as compound A43D; however, modified at the C3 position instead of C28 give HIV-1 maturation inhibitor such as bevirimat. Bevirimat exhibited promising pharmacokinetic profiles in clinical trials, but its effectiveness was compromised by the high baseline drug resistance of HIV-1 variants with polymorphism in the putative drug binding site. In an effort to determine whether the viruses with bevirimat resistant polymorphism also altered their sensitivities to the betulinic acid derivatives that inhibit HIV-1 entry, a series of new betulinic acid entry inhibitors were synthesized and tested for their activities against HIV-1 NL4-3 and NL4-3 variants resistant to bevirimat. The results show that the bevirimat resistant viruses were approximately 5- to10-fold more sensitive to three new glutamine ester derivatives (13, 15 and 38) and A43D in an HIV-1 multi-cycle replication assay. In contrast, the wild type NL4-3 and the bevirimat resistant variants were equally sensitive to the HIV-1 RT inhibitor AZT. In addition, these three new compounds markedly improved microsomal stability compared to A43D.

Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors

Wepreviously reported that [[N-[3β-hydroxyllup-20(29)-en-28-oyl]-7- aminoheptyl]carbamoyl]methane (A43D, 4) was a potent HIV-1 entry inhibitor. However, 4 was inactive against HIV-2 virus, suggesting the structural requirements for targeting these two ret

Betulinic acid derivatives: A new class of specific inhibitors of human immunodeficiency virus type 1 entry

A novel series of ω-aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). The anti-HIV-1 activity of several members of this new series was found to be in the nanomolar range in CEM 4 and MT-4 cell cultures. The optimization of the ω-aminoalkanoic acid side chain is described. The presence of an amide function within the side chain was found important for optimal activity. RPR 103611 (14g), a statine derivative, was found to be inactive against HIV-1 protease, reverse transcriptase, and integrase as well as on gp120/CD4 binding. 'Time of addition' experiments suggested interaction with an early step of HIV-1 replication. As syncytium formation, but not virus-cell binding, seems to be affected, betulinic acid derivatives are assumed to interact with the postbinding virus-cell fusion process.

Lupane derivatives, their preparation and the pharmaceutical compositions which contain them

The present invention relates to new lupane dervivatives of the general formula: STR1 to their salts, to their preparation and to the pharmaceutical compositions which contain them.