39172-32-2

Usage

Type of compound

Brominated derivative of dioxolane (a cyclic ether compound)

Uses

Intermediate in the synthesis of various compounds used in pharmaceutical and pesticide products; building block in organic synthesis and chemical research

Unique property

Presence of the bromine atom, which gives it unique reactivity and properties valuable in the development of new materials and substances.

InChI:InChI=1/C10H11BrO2/c1-10(12-5-6-13-10)8-3-2-4-9(11)7-8/h2-4,7H,5-6H2,1H3

Upstream product

• 107-21-1 ethylene glycol 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 203443-01-0 6-methoxy-2-[3-(2-methyl-1,3-dioxolan-2-yl)phenyl]-3,4-dihydronaphthalene 
• 132100-31-3 3-(2-methyl-[1,3]dioxolan-2-yl)benzaldehyde 
• 60283-15-0 1-(3-acetylphenyl)-2,2,2-trifluoroethan-1-one 
• 864147-97-7 1-[3-(2-methyl-3-phenyl-allyl)-phenyl]-ethanone 
• 568572-28-1 1-[3-(3-phenyl-allyl)-phenyl]-ethanone 
• 107484-93-5 C₁₀H₁₁BrMgO₂ 
• 203443-13-4 6-Methoxy-2-[3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl]-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 203443-11-2 6-Methoxy-2-[3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl]-3,4-dihydro-2H-naphthalen-1-one 
• 22071-15-4 ketoprofen 
• 17983-62-9 1-[3-(trimethylsilyl)phenyl]ethanone 
• 51498-07-8 2-(3-biphenylyl)propanoic acid 
• 22161-81-5 S-ketoprofen 
• 173652-77-2 (2R,3S)-3-(3'-bromophenyl)butane-1,2-diol 

Relevant academic research and scientific papers

Chemo- and Stereoselective Synthesis of Fluorinated Amino Alcohols through One-pot Reactions using Alcohol Dehydrogenases and Amine Transaminases

A series of amino alcohols have been prepared in a chemo-, diastereo- and enantioselective fashion starting from the corresponding (het)aryl diketones, avoiding tedious chemical protection and deprotection steps. Different alcohol dehydrogenases have been

Chemo- and enantioselective routes to chiral fluorinated hydroxyketones using ketoreductases

Chiral fluorinated hydroxyketones were synthesized with excellent ee (>98%) and yield by a chemo- and stereoselective reduction of prochiral methyl/trifluoromethyl diketones using commercially available ketoreductase enzymes. By using p- and m-trifluoroac

Stereoselective Bioreduction of Telluro-Acetophenones to Optically Active Hydroxy Tellurides

Organotellurium compounds exhibit a broad range of useful applications in organic synthesis, materials science and medicinal chemistry fields. Despite their increasing applicability, the synthesis of enantiomerically pure organotellurium compounds remains nowadays scarcely reported in the literature. Herein, the chemical synthesis and biocatalyzed reductions of a set of telluro-acetophenones using both (R) and (S)-selective alcohol dehydrogenases (ADHs) is described for the first time, obtaining enantiomerically enriched hydroxy tellurides with excellent selectivities under very mild reaction conditions. On the one hand, enantiopure para-substituted (S)-hydroxy tellurides were obtained using the Ras-ADH (77–95 % conversion) and ADH-A (52–75 %), the ADH-A leading to the enantiopure (S)-hydroxy tellurides substituted at the meta-position (69–75 %). On the other hand, the evo-1.1.200 displayed high selectivity towards the preparation of optically alcohols with substitutions at the para-position of the aromatic ring (60–68 % conversion and 92–97 % ee), while the Lb-ADH led to the best results when reducing bulky ketones at the meta-position (79–82% conversion and 88–99 % ee).

Synthesis, Antioxidant Activity and Cytotoxicity of N-Functionalized Organotellurides

The use of antioxidants is the most effective means to protect the organism against cellular damage caused by oxidative stress. In this context, organotellurides have been described as promising antioxidant agents for decades. Herein, a series of N-functionalized organotellurium compounds has been tested as antioxidant and presented remarkable activities by three different in vitro chemical assays. They were able to reduce DPPH[rad] radical with IC50 values ranging from 5.08 to 19.20 μg mL?1, and some of them also reduced ABTS[rad]+ radical and TPTZ-Fe3+ complex in ABTS[rad]+ and FRAP assays, respectively. Initial structure-activity relationship discloses that the nature of N-substituent strongly influenced both activity and cytotoxicity of the studied compounds. Furthermore, radical scavenging activities of N-functionalized organotellurides have been compared with those of their selenilated congeners, demonstrating that the presence of tellurium atom has an essential role in antioxidant activity.

Diacetal Ditellurides as Highly Active and Selective Antiparasitic Agents toward Leishmania amazonensis

Leishmaniasis is a neglected tropical disease and a public health concern in at least 98 countries, affecting mainly the poorest populations. Pharmaceuticals and chemotherapies available for leishmaniasis treatment have several limitations, which clearly justify the efforts to find new potential antileishmanial drugs. In this context, antiprotozoal activities toward different Leishmania species have been reported for hypervalent tellurium compounds, which motivated us to investigate, for the first time, the leishmanicidal properties of some nonhypervalent diaryl ditellurides. Thus, this work describes in vitro activity against Leishmania amazonensis and the cytotoxicities of diaryl ditellurides. Ditelluride LQ7 revealed a strong leishmanicidal activity on promastigotes and amastigotes at submicromolar levels (IC50 = 0.9 ± 0.1 and 0.5 ± 0.1 μmol L-1, respectively) and presented selectivity indexes greater than those of reference drug miltefosine. This preliminary study suggests that diaryl ditellurides may be promising scaffolds for the development of new agents for leishmaniasis treatment.

Straightforward microwave-assisted synthesis of organochalcogen amines by reductive amination

Organoselenium and organotellurium amines have been shown to present a broad range of interesting properties for both synthetic and biological applications. Despite the current interest in this class of compounds, only few methods to access organochalcogen amines are described in literature, most which involve restrictive conditions associated with displacement reaction, metal-assisted reactions or enzymatic approach. In general, these methods produce organochalcogen amines in poor yields, by long reactions that require protective groups. In this regard, a set of aryl chalcogen (Se, Te) amines were prepared by reductive amination employing a microwave-assisted one-pot protocol. This approach offered a convenient and versatile method to synthesize primary and secondary organochalcogen amines with significantly short time reactions (5–10 min) and satisfactory yields (40–89%).

Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors

Retinoic acid receptor (RAR)-related orphan receptors (RORs) regulate a variety of physiological processes, including hepatic gluconeogenesis, lipid metabolism, circadian rhythm and immune function. The RAR agonist: all-trans retinoic acid was reported to be an RORβ inverse agonist, but no information is available regarding ROR activity of its synthetic analogue Am580. Therefore, we screened Am580 and some related tetramethyltetrahydronaphthalene derivatives and carried out structural development studies, including substitution of carbon atoms with silicon, with the aim of creating a potent ROR transcriptional inhibitor. The phenyl amide disila compound 22 showed the most potent ROR-inhibitory activity among the compounds examined. Its activity towards RORα, RORβ and RORγ was increased compared to that of Am580. The IC50 values for RORα, RORβ and RORγ are 1.3, >10 and 4.5 μM, respectively.

OXAZOLE AND THIAZOLE DERIVATIVES AS ALX RECEPTOR AGONISTS

The invention relates to oxazole and thiazole derivatives of formula (I), wherein A, E, X, R1 and R2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.

Triphenylbutanamines: Kinesin spindle protein inhibitors with in vivo antitumor activity

The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-l-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit Kiapp ≥ 10 nM and GI50 ≈ 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

OXAZOLE AND THIAZOLE DERIVATIVES AS ALX RECEPTOR AGONISTS

The invention relates to oxazole and thiazole derivatives of formula (I), wherein A, E, X, R1 and R2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.