55029-05-5

Upstream product

• 473-98-3 betulin 
• 43124-92-1 (?)-3β,28-diacetoxydihydrobetulin 
• 54145-78-7 (1S,3a5,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde 
• 79875-75-5 6β,28-diacetoxylup-20(29)-en-3-one 
• 79875-65-3 6β,28-dihydroxy-3-oxolup-20(29)-ene 
• 1721-69-3 betulin diacetate 
• 43124-92-1 3β,28-Diacetoxylupane 
• 1072913-62-2 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol 
• 1721-69-3 betulin diacetate 
• 81346-04-5 3β,28-lupanediol 28-acetate 

Downstream Products

• 25576-27-6 3-oxolupan-28-ic acid 
• 43124-92-1 (?)-3β,28-diacetoxydihydrobetulin 
• 25576-27-6 Lupanon-⁽³⁾-carbonsaeure-⁽²⁸⁾ 
• 134501-93-2 17α(H)-28-Norlupane 
• 134501-93-2 17β(H)-28-Norlupane 
• 134502-04-8 3-Oxolupane tosylhydrazone 
• 464-99-3 Lupane 
• 3186-72-9 3-Oxolupane 
• 3186-86-5 3β-Hydroxy-28-lupane 
• 43124-92-1 3β,28-Diacetoxylupane 
• 1007345-51-8 C₄₉H₇₆N₂O₅ 
• 1393571-37-3 3-O,28-O-diphthaloyl dihydrobetulin 
• 20066-05-1 methyl dihydrobetulonate 
• 38736-78-6 dihydrobetulinic acid 

Relevant academic research and scientific papers

Preparation of a 24-nor-1,4-dien-3-one triterpene derivative from betulin: A new route to 24-nortriterpene analogues

A new route to 24-nortriterpene derivatives with 2-hydroxy-δ1,4-cyclohexadieny-3-one A-rings from triterpene precursors has been demonstrated beginning with betulin to prepare derivatives of betulinic acid. The key steps in the transformation are a Suarez cleavage of the A-ring with a subsequent SM12-mediated pinacol-type coupling to reclose the A-ring following removal of the C-24 carbon by oxidative cleavage.

Rearrangements of the Betulin Core. Synthesis of Terpenoids Possessing the Bicyclo[3.3.1]nonane Fragment by Rearrangement of Lupane-Type Epoxides

The rearrangements of dihydrobetulin, dihydrobetulinic acid, and abeo-lupane epoxides under acidic conditions (HCl, montmorillonite K10, and BF3·Et2O) were studied. The treatment of dihydrobetulin with HCl or K10 produced abeo-lupane olefins. Their epoxid

Electrosynthesis of Stable Betulin-Derived Nitrile Oxides and their Application in Synthesis of Cytostatic Lupane-Type Triterpenoid-Isoxazole Conjugates

Novel lupane-type triterpenoid-isoxazole conjugates were designed by direct placing of isoxazole linker at C(17) of triterpenoid. The suggested synthetic sequence demonstrates successful combination of electro-organic synthesis and conventional approaches. TEMPO-mediated electrooxidation of betulin to betulinal was developed and optimized at boron-doped diamond anodes with potassium acetate as inexpensive supporting electrolyte. Betulinal-derived oxime was further selectively electro-oxidized at a graphite anode to nitrile oxide, which proved to be stable and isolable species. The same reaction sequence was performed with 3β-lupane-3,28-diol. Nitrile oxides were characterized by 15N NMR and X-ray crystallography. The isolable nitrile oxides allowed creation of isoxazole library by 1,3-dipolar cycloaddition reactions with various alkynes. Some of the title conjugates exhibit cytostatic properties against breast cancer cell line MCF7, glioblastoma multiform cell line U-87 MG and lung carcinoma cell line A549 with growth inhibition (GI50) concentrations up to 11 μm, while being harmless to immortalized human fibroblasts hTERT (GI50 >100 μm).

Synthesis and Antimicrobial Activity of Dihydrobetulin N-Acetylglucosaminides

Dihydrobetulin N-acetylglucosaminides were synthesized for the first time. A study of their antimicrobial activity against a standard set of Gram-positive and Gram-negative bacteria and fungi showed highly selective bacteriostatic activity for glycosides 9 and 13 against Staphylococcus aureus ATCC 209p.

First conjugate of glucuronic acid with triterpenoid dihydrobetulin

3β-O-Acetyl-28-O-succinyl-(2,3,4-tri-O-acetyl-5-methoxycarbonyl-β-D-glucopyranosyl)dihydrobetulin was synthesized.

EXTENDED BETULINIC ACID ANALOGS

Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors, as represen

Novel betulin derivatives as antileishmanial agents with mode of action targeting type IB DNA topoisomerase

Toward developing antileishmanial agents with mode of action targeted to DNA topoisomerases of Leishmania donovani, we have synthesized a large number of derivatives of betulin. The compound, a natural triterpene isolated from the cork layer of Betula spp. plants exhibits several pharmacological properties. Three compounds (disuccinyl betulin, diglutaryl dihydrobetulin, and disuccinyl dihydrobetulin) inhibit growth of the parasite as well as relaxation activity of the enzyme type IB topoisomerase [Leishmania donovani topoisomerase I (LdTOP1LS)] of the parasite. Mechanistic studies suggest that these compounds interact with the enzyme in a reversible manner. The stoichiometry of these compounds binding to LdTOP1LS is 1:1 (mole/mole) with a dissociation constant on the order of ～10-6 M. Unlike CPT, these compounds do not stabilize the cleavage complex; rather, they abrogate the covalent complex formation. In processive mode of relaxation assay condition, these compounds slow down the strand rotation event, which ultimately affects the relaxation of supercoiled DNA. It is noteworthy that these compounds reduce the intracellular parasite burden in macrophages infected with wild-type L. donovani as well as with sodium antimony gluconate resistant parasite (GE1). Taken together, our data suggest that these betulin derivatives can be exploited as potential drug candidates against threatening drug resistant leishmaniasis. Copyright

N'--3-AMINO-3-PHENYLPROPEONIC ACID AND THE PHARMACEUTICALLY ACCEPTABLE DERIVATIVES THEREOF, A METHOD FOR THE PRODUCTION AND THE USE THEREOF IN THE FORM OF A MEDICINAL AGENT

The invention relates to the field of organic chemistry and medicine, in particular to virology. More specifically the invention relates to a novel chemical compound N′-{N-[3-oxo-lupan-28-oyl]-9-aminononanoyl}-3-amino-3-phenylpropionic acid of formula 1 and to pharmaceutically acceptable salts and prodrug forms thereof exhibiting an anti-viral (anti-HIV) and immunostimulating activity. A method for producing the compound of formula 1 and the use thereof for the manufacture of a medicinal agent exhibiting an anti-viral (anti-HIV) and immunostimulating activity is also disclosed.

Betulin-derived compounds as inhibitors of alphavirus replication

This paper describes inhibition of Semliki Forest virus (SFV) replication by synthetic derivatives of naturally occurring triterpenoid betulin (1). Chemical modifications were made to OH groups at C-3 and C-28 and to the C-20-C-29 double bond. A set of heterocyclic betulin derivatives was also assayed. A free or acetylated OH group at C-3 was identified as an important structural contributor for anti-SFV activity, 3,28-di-O-acetylbetulin (4) being the most potent derivative (IC50 value 9.1 μM). Betulinic acid (13), 28-O-tetrahydropyranylbetulin (17), and a triazolidine derivative (41) were also shown to inhibit Sindbis virus, with IC50 values of 0.5, 1.9, and 6.1 μM, respectively. The latter three compounds also had significant synergistic effects against SFV when combined with 3′-amino-3′-deoxyadenosine. In contrast to previous work on other viruses, the antiviral activity of 13 was mapped to take place in virus replication phase. The efficacy was also shown to be independent of external guanosine supplementation.

Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin

The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.