13159-28-9

Usage

Uses

Used in Pharmaceutical Industry:
Betulinic aldehyde is used as a pharmaceutical agent for its antitumor properties, making it a potential candidate for the development of anticancer drugs. Its anti-inflammatory, antimalarial, and antimicrobial activities also contribute to its potential applications in the treatment of various diseases and conditions.
Used in Drug Development:
Betulinic aldehyde is used as a lead compound in drug development due to its potent inhibitory effects on certain enzymes. Its diverse biological activities and potential as an anti-viral and anti-HIV agent make it a valuable subject of ongoing investigation for the creation of novel therapeutic agents.
Used in Medicinal Chemistry Research:
Betulinic aldehyde is utilized as a subject of study in medicinal chemistry research to explore its potential applications and mechanisms of action. Its extensive research and diverse biological activities contribute to the advancement of knowledge in the field and the development of new therapeutic strategies.

InChI:InChI=1/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32H,1,8-17H2,2-7H3

Upstream product

• 27570-21-4 3-O-acetylbetulinal 
• 472-15-1 Betulinic acid 
• 473-98-3 betulin 
• 1025068-55-6 (3β)-3-acetyloxy-N-methoxy-N-methyl-lup-20(29)-en-28-amide 
• 212708-99-1 O,O'-bis-(trimethylsilyl)-betulin 
• 1587722-29-9 3-O-allyl betulinal 
• 10376-50-8 3-O-acetylbetulinic acid 
• 59868-82-5 3-O-acetylbetulinic acid chloride 
• 1721-69-3 betulin diacetate 
• 27570-20-3 betulin monoacetate 
• 473-98-3 3β,28-dihydroxy-lup-20(29)-ene 

Downstream Products

• 472-15-1 Betulinic acid 
• 1025069-19-5 (3β)-3-[4-(2-phenylmethoxycarbonyl)-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-al 
• 1228273-12-8 (R)-4-[3β-hydroxy-28-norlup-20(29)-en-17β-yl]-γ-butyrolactone 
• 473-98-3 betulin 
• 4481-62-3 betulonic acid 
• 545-47-1 lupenol 
• 1025068-98-7 4-fluoro-N-[[(3β)-3-hydroxylup-20(29)-en-28-yl]methyl]phenylacetamide 
• 1025069-18-4 (3β)-28-[[(phenylcarbonyl)amino]methyl]lup-20(29)-en-3-ol; hydrogen 3,3-dimethylpentanedioate 
• 1025068-79-4 [(3β)-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetic acid 
• 1025068-78-3 methyl [(3β)-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetate 
• 1025069-17-3 (3β)-28-[[(phenylcarbonyl)amino]methyl]lup-20(29)-en-3-ol; methyl 3,3-dimethylpentanedioate 
• 1025069-72-0 (3β)-28-[[[(2-(4-fluorophenyl)-1-oxo)ethyl]amino]methyl]lup-20(29)-en-3-ol; hydrogen 3,3-dimethylpentanedioate 
• 1025070-12-5 [(3β)-N-(2-hydroxy-1,1-dimethylethyl)-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetamide 
• 1025068-99-8 (3β)-28-[[[[2-(4-fluorophenyl)-1-oxo]ethyl]amino]methyl]lup-20(29)-en-3-ol; 2-trimethylsilylethyl 3,3-dimethylpentanedioate 

Relevant academic research and scientific papers

POTENTIAL ALLELOPATHIC LUPANE TRITERPENES FROM BIOACTIVE FRACTIONS OF MELILOTUS MESSANENSIS

The aerial parts of Melilotus messanenis (sweet clover) afforded, from the medium polar bioactive fractions, in addition to the known lupane triterpenes lupeol, betulin, betulin aldehyde and betulinic acid, the new norlupane messagenin (30-norlupane-3β,28-diol-20-one) which have been tested as allelochemicals.Structures and their stereochemistries were elucidated by spectral methods and chemical transformations.Messagenin has been synthesized from betulinic acid.The effect of a series of aqueous solutions at 10-4-10-9 M of eight natural and synthetic lupane derivatives were tested for their effects on the germination and growth of the dicotyledon species Lactuca sativa and Lepidium sativum and the monocotyledon species Hordeum vulgare and Triticum aestivum.All eight lupane triterpenes possess potential allelopathic activity in particular over dicotyledon species and they are likely to be significantly involved in the alleopathic action of Melilotus messanensis. - Key words: Melilotus messanensis; Leguminoseae; Fabaceae; sweet clover; lupane triterpenes; messagenin; 30-nor-lupane-3β,28-diol-20-one; allelopathy; Lactuca sativa; lepidium sativa; Hordeum vulgare; Triticum aestivum.

Alkyl amine bevirimat derivatives are potent and broadly active HIV-1 maturation inhibitors

Concomitant with the release of human immunodeficiency virus type 1 (HIV-1) particles from the infected cell, the viral protease cleaves the Gag polyprotein precursor at a number of sites to trigger virus maturation. We previously reported that a betulinic acid-derived compound, bevirimat (BVM), blocks HIV-1 maturation by disrupting a late step in protease-mediated Gag processing: the cleavage of the capsid-spacer peptide 1 (CA-SP1) intermediate to mature CA. BVM was shown in multiple clinical trials to be safe and effective in reducing viral loads in HIV-1-infected patients. However, naturally occurring polymorphisms in the SP1 region of Gag (e.g., SP1-V7A) led to a variable response in some BVM-treated patients. The reduced susceptibility of SP1-polymorphic HIV-1 to BVM resulted in the discontinuation of its clinical development. To overcome the loss of BVM activity induced by polymorphisms in SP1, we carried out an extensive medicinal chemistry campaign to develop novel maturation inhibitors. In this study, we focused on alkyl amine derivatives modified at the C-28 position of the BVM scaffold. We identified a set of derivatives that are markedly more potent than BVM against an HIV-1 clade B clone (NL4-3) and show robust antiviral activity against a variant of NL4-3 containing the V7A polymorphism in SP1. One of the most potent of these compounds also strongly inhibited a multiclade panel of primary HIV-1 isolates. These data demonstrate that C-28 alkyl amine derivatives of BVM can, to a large extent, overcome the loss of susceptibility imposed by polymorphisms in SP1.

Preparation of Betulone Via Betulin Oxidation Over Ru Nanoparticles Deposited on Graphitic Carbon Nitride

Derivatives of betulin obtained by oxidation have broad pharmacological applications, demonstrating anti-inflammatory, antioxidant, hepatoprotective, and anticancer activity. Ru supported catalysts based on graphitic carbon nitride or N-doped carbon were prepared via a mild reduction of the initial Ru precursor with hydrazine. These catalysts along with Ru supported on carbon nanofibers and a mesoporous carbon support Sibunit were studied in catalytic oxidation of betulin. Ru/carbon nitride demonstrated catalytic activity in betulin oxidation higher than Ru/N-doped carbon (conversion of betulin up to ca. 70% and 30%, respectively). Selectivity to different oxidation products was dependent on the properties of the carbon supports.

Synthesis and biological activity of new homolupanes and homolupane saponins

A concise synthesis of 28a-homolupane triterpenes and the corresponding saponins containing d-mannose, d-idose, d-arabinose, and l-rhamnose moieties was elaborated. The overall synthesis of the new triterpenes involved three linear steps starting from readily available 3-O-acetyl-betulinal: elongation of the carbon chain by Wittig reaction followed by enol ether hydrolysis and reduction (or oxidation) of the elongated aldehyde. Saponins were obtained by glycosylation of triterpenes with classical Schmidt donors. Cytotoxic activities of new lupane and homolupane compounds were evaluated in vitro. Several triterpenes and the corresponding saponins exhibited an interesting cytotoxic activity profile against human cancer cell lines. Influence of the side-chain structure and substituents on the cytotoxicity of betulin and homobetulin derivatives was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds.

Selective oxidation of betulin by Cr(VI) reagents

Oxidation of betulin by pyridinium dichromate, pyridinium chlorochromate, and K2Cr2O7 - H2SO4 in the presence of tetrabutylammonium bromide was studied. Products of regioselective C-3, C-28-, and exha

Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and function

Development of mitochondrially-targeted drugs is receiving increasing attention because of the central roles these organelles play in energy production, reactive oxygen generation, and regulation of cell death pathways. Previous studies have demonstrated that both natural and synthetic triterpenoids can disrupt mitochondrial structure and function. In this study, we tested the ability of a number of dimethylaminopyridine (DMAP) derivatives of lupane triterpenoids to target mitochochondria in two human melanoma cell lines and an untransformed normal fibroblast line. These compounds induced a striking fragmentation and depolarization of the mitochondrial network, along with an inhibition of cell proliferation. A range of potencies among these compounds was noted, which was correlated with the number, position, and orientation of the DMAP groups. Overall, the extent of proliferation inhibition mirrored the effectiveness of mitochondrial disruption. Thus, DMAP derivatives of lupane triterpenoids can be potent mitochondrial perturbants that appear to suppress cell growth primarily via their mitochondrial effects.

Selective oxidation of betulin for the preparation of betulinic acid, an antitumoral compound

This paper describes a semisynthetic approach for the preparation of betulinic acid from betulin. The main step of this synthetic approach is the selective oxidation of primary alcohol function of betulin. This reaction is accomplished with chromic oxide adsorbed on silica gel to obtain betulinal in an adequate yield. Betulinal is then almost quantitatively oxidized to betulinic acid by potassium permanganate action.

Oxidation of a wood extractive betulin to biologically active oxo-derivatives using supported gold catalysts

Betulin (90-94%) was extracted from birch with a non-polar solvent and recrystallized from 2-propanol. Liquid-phase oxidation of betulin aimed at obtaining its biologically active oxo-derivatives (betulone, betulonic and betulinic aldehydes), exhibiting e.g. antitumor, anti-inflammatory, antiparasitic, anticancer and anti-HIV properties, was demonstrated for the first time over gold-based catalysts. Gold was deposited on pristine TiO2 and the same support modified with ceria and lanthana, followed by pretreatment with a H2 or O2 atmosphere. The catalysts were characterized by XRD, BET, ICP, TEM, XPS, DRIFT CO, TPD of NH3 and CO2 methods. The nature of the support, type of modification and the pretreatment atmosphere through the metal-support interactions significantly influenced the average particle size of gold, its distribution and the electronic state of gold, as well as the acid-base properties and, thereby, the catalytic performance (activity and selectivity) in betulin oxidation. Au/La2O3/TiO2 pretreated in H2 displayed the highest catalytic activity in betulin oxidation among the studied catalysts with selectivities to betulone, betulonic and betulinic aldehydes of 42, 32 and 27%, respectively, at 69% conversion. Side reactions resulting in oligomerization/polymerization products occurred on the catalyst surface with the participation of strong acid sites, diminishing the yield of the desired compounds. The latter was improved by adding hydrotalcite with the basic properties to the reaction mixture containing the catalyst. Kinetic modelling through numerical data fitting was performed to quantify the impact of such side reactions and determine the values of rate constants.

Synthesis of betulinic acid derivatives with activity against human melanoma

Betulinic acid has been modified at C-3, C-20, and C-28 positions and the toxicity of the derivatives has been evaluated against cultured human melanoma (MEL-2) and human epidermoid carcinoma of the mouth (KB) cell lines. This preliminary investigation demonstrates that simple modifications of the parent structure of betulinic acid can produce potentially important derivatives, which may be developed as antitumor drugs.

Oxidative transformations of betulinol

Starting from commercially available betulinol by a combination of several selective oxidation procedures betutinal, betulinic acid, betulonal as well as betulonic acid were obtained in high yields on a multi-gram scale.