Month: January 2023

Exploratory study of photocyclization reactions of N-(trimethylsilylmethylthioalkyl)phthalimides was written by Yoon, Ung Chan;Lee, Sang Jin;Lee, Kyung Ja;Cho, Sung Ju;Lee, Chan Woo;Mariano, Patrick S.. And the article was included in Bulletin of the Korean Chemical Society in 1994.Computed Properties of C13H14BrNO2 This article mentions the following:

Single electron transfer (SET) induced photocyclization of N-(trimethylsilylmethylthioalkyl)phthalimides I (n = 2-6) were studied in methanol and acetone. Photocyclizations in methanol produced modest to high yields of products such as II. A singlet SET pathway dominates in methanol while a triplet process dominates in acetone. The efficient and regioselective cyclization reactions observed for photolyses in methanol represent synthetically useful processes for construction of medium and large ring heterocyclic compounds In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Computed Properties of C13H14BrNO2).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Computed Properties of C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Difluorocarbene-Derived Trifluoromethylthiolation and [¹⁸F]Trifluoromethylthiolation of Aliphatic Electrophiles was written by Zheng, Jian;Wang, Lu;Lin, Jin-Hong;Xiao, Ji-Chang;Liang, Steven H.. And the article was included in Angewandte Chemie, International Edition in 2015.Name: 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

The first trifluoromethylthiolation and [¹⁸F]trifluoromethylthiolation of alkyl electrophiles with in situ generated difluorocarbene in the presence of elemental sulfur and external (radioactive) fluoride ion is described. This transition-metal-free approach is high yielding, compatible with a variety of functional groups, and operated under mild reaction conditions. The conceptual advantage of this exogenous-fluoride-mediated transformation enables unprecedented syntheses of [¹⁸F]CF₃S-labeled mols. from most commonly used [¹⁸F]fluoride ions. The rapid radiochem. reaction time (â‰? min) and high functional-group tolerance allow access to a variety of aliphatic [¹⁸F]CF₃S compounds in high yields. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Name: 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Name: 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Biphenyl Pyridazinone Derivatives as Inhaled PDE4 Inhibitors: Structural Biology and Structure-Activity Relationships was written by Gracia, Jordi;Buil, Maria Antonia;Castro, Jordi;Eichhorn, Peter;Ferrer, Manel;Gavalda, Amadeu;Hernandez, Begona;Segarra, Victor;Lehner, Martin D.;Moreno, Imma;Pages, Lluis;Roberts, Richard S.;Serrat, Jordi;Sevilla, Sara;Taltavull, Joan;Andres, Miriam;Cabedo, Judit;Vilella, Dolors;Calama, Elena;Carcasona, Carla;Miralpeix, Montserrat. And the article was included in Journal of Medicinal Chemistry in 2016.Electric Literature of C8H6BrFO2 This article mentions the following:

Cyclic nucleotide cAMP is an ubiquitous second messenger involved in a plethora of cellular responses to biol. agents involving activation of adenylyl cyclase. Its intracellular levels are tightly controlled by a family of cyclic nucleotide degrading enzymes, the PDEs. In recent years, cyclic nucleotide phosphodiesterase type 4 (PDE4) has aroused scientific attention as a suitable target for anti-inflammatory therapy in respiratory diseases, particularly in the management of asthma and COPD. Here the authors describe efforts to discover novel, highly potent inhaled inhibitors of PDE4. Through structure based design, with the intervention of a wide variety of functional groups and physichochem. profiles to occupy the solvent-filled pocket of the PDE4 enzyme, the authors modified the structure of the authors’ oral PDE4 inhibitors to reach compounds up to picomolar enzymic potencies. In vitro potencies were demonstrated in a rat lung neutrophilia model by suspension microspray administration. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6Electric Literature of C8H6BrFO2).

Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Electric Literature of C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Identification of Human Alanine-Glyoxylate Aminotransferase Ligands as Pharmacological Chaperones for Variants Associated with Primary Hyperoxaluria Type 1 was written by Grottelli, Silvia;Annunziato, Giannamaria;Pampalone, Gioena;Pieroni, Marco;Dindo, Mirco;Ferlenghi, Francesca;Costantino, Gabriele;Cellini, Barbara. And the article was included in Journal of Medicinal Chemistry in 2022.Application of 14425-64-0 This article mentions the following:

Primary hyperoxaluria type I (PH1) is a rare kidney disease due to the deficit of alanine:glyoxylate aminotransferase (AGT), a pyridoxal-5′-phosphate-dependent enzyme responsible for liver glyoxylate detoxification, which in turn prevents oxalate formation and precipitation as kidney stones. Many PH1-associated missense mutations cause AGT misfolding. Therefore, the use of pharmacol. chaperones (PCs), small mols. that promote correct folding, represents a useful therapeutic option. To identify ligands acting as PCs for AGT, we first performed a small screening of com. available compounds We tested each mol. by a dual approach aimed at defining the inhibition potency on purified proteins and the chaperone activity in cells expressing a misfolded variant associated with PH1. We then performed a chem. optimization campaign and tested the resulting synthetic mols. using the same approach. Overall, the results allowed us to identify a promising hit compound for AGT and draw conclusions about the requirements for optimal PC activity. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Application of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Modular synthesis of stereodefined benzocyclobutene derivatives via sequential Cu- and Pd-catalysis was written by Talbot, Fabien J. T.;Zhang, Shibo;Satpathi, Bishnupada;Howell, Gareth P.;Perry, Gregory J. P.;Crisenza, Giacomo E. M.;Procter, David J.. And the article was included in ACS Catalysis in 2021.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

Benzocyclobutenes (BCBs) are of growing interest in materials and medicinal chem., although general routes for their provision remain underexplored. A modular, divergent and stereoselective Cu- and Pd-catalyzed assembly/cyclization sequence allows the synthesis of densely functionalized BCBs, from readily accessible imine, allene and diboron precursors. Preliminary results have identified enantioselective conditions for this protocol, and highlighted, for example, its applicability to the synthesis of BCB-containing peptides. By simple variation of exptl. conditions or substrate modification, authors strategy was expanded to deliver indoline and quinoline derivatives, suitable for further manipulations. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ruthenium-Catalyzed Intramolecular Hydroarylation of Arenes with Olefins in Water was written by Mukherjee, Kallol;Ramesh, E.;Ghosh, Koushik;Sahoo, Akhila K.. And the article was included in Asian Journal of Organic Chemistry in 2018.Reference of 192810-12-1 This article mentions the following:

Herein, A Ru-catalyzed intramol. hydroarylation of arenes I (R = H, 4-Me, 3-Br, etc.; R¹ = Me; R² = Me, Et; MPS = Me Ph sulfoximine) in an aqueous medium is presented. With the aid of Me Ph sulfoximine or an amide directing group, this atom-efficient hydroarylation of arenes ensued dihydrobenzofuran derivatives II (R = H, 5-Me, 6-OBn, etc.; R¹ = Me; R² = Me, Et; MPS = Me Ph sulfoximine). Sequential double hydroarylation of arene motifs resulted in highly peripheral-decorated heterocycles. Deuterium labeling studies and control experiments offer valuable information in understanding the reactivity and the mechanistic data. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1Reference of 192810-12-1).

Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Reference of 192810-12-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Activity Relationship Studies of Pyrrolone Antimalarial Agents was written by Murugesan, Dinakaran;Kaiser, Marcel;White, Karen L.;Norval, Suzanne;Riley, Jennifer;Wyatt, Paul G.;Charman, Susan A.;Read, Kevin D.;Yeates, Clive;Gilbert, Ian H.. And the article was included in ChemMedChem in 2013.COA of Formula: C9H11BrO This article mentions the following:

Previously reported pyrrolones, such as TDR32570 (I), exhibited potential as antimalarial agents; however, while these compounds have potent antimalarial activity, they suffer from poor aqueous solubility and metabolic instability. Here, further structure-activity relationship studies are described that aimed to solve the developability issues associated with this series of compounds In particular, further modifications to the lead pyrrolone, involving replacement of a Ph ring with a piperidine and removal of a potentially metabolically labile ester by a scaffold hop, gave rise to derivatives with improved in vitro antimalarial activities against Plasmodium falciparum K1, a chloroquine- and pyrimethamine-resistant parasite strain, with some derivatives exhibiting good selectivity for parasite over mammalian (L6) cells. Three representative compounds were selected for evaluation in a rodent model of malaria infection, and the best compound showed improved ability to decrease parasitemia and a slight increase in survival. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0COA of Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.COA of Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Stereochemical effects in cyclopropane ring openings: biomimetic ring openings of all isomers of 22,23-methylenecholesterol acetate was written by Zimmerman, Mary P.;Li, Hui Ting;Duax, William L.;Weeks, Charles M.;Djerassi, Carl. And the article was included in Journal of the American Chemical Society in 1984.Name: Isopentyltriphenylphosphonium bromide This article mentions the following:

By using the unique stereochem. of the side chain in cholesterol, the dynamic influence of proximate chiral centers on the acid-promoted isomerizations of cyclopropanes is defined. Unexpectedly, when the cyclopropane is placed in the 22,23 position, either a backbone rearrangement is induced or unanticipated side-chain olefins arise, each dependent on the stereochem. of the cyclopropane starting material. The synthesis and stereochem. assignments of the 4 possible 22,23-methylenecholesterol acetates I are reported as well as the effect of stereochem. on the acid-promoted isomerization of these compounds [22R,23R]-I and [22S,23S]-I under the conditions of ring opening yield unexpected backbone rearrangement products, i.e., acetoxydimethylnorcholestadienes II, which can also be obtained from rearrangements of methylcholestadienol acetates III and IV. The stereochem. criteria governing the course of these isomerizations are discussed. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Name: Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Name: Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Total Synthesis of (-)-Blepharocalyxin D and Analogues was written by Cons, Benjamin D.;Bunt, Adam J.;Bailey, Christopher D.;Willis, Christine L.. And the article was included in Organic Letters in 2013.Formula: C9H11BrO This article mentions the following:

An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analog is described. The key step involves an acid-mediated cascade process in which reaction of Me 3,3-dimethoxypropanoate with γ,δ-unsaturated alcs. possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

para-Bromination of aromatic amines: 4-bromo-N,N-dimethyl-3-(trifluoromethyl)aniline was written by Fox, G. J.;Hallas, G.;Hepworth, J. D.;Paskins, K. N.. And the article was included in Organic Syntheses in 1976.Name: 3,4-Dibromoaniline This article mentions the following:

Treatment of m-F3CC6H4NMe2 with 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one (from 2,4,6-Br3C6H2OH and Br) in CH2Cl2 gave 82-90% 4,3-Br(F3C)C6H3NMe2. Twenty-eight addnl. arom amines, e.g., 2-ClC6H4NH2, PhNH2, 1-naphthylamine, and o-anisidine, were para brominated in a similar manner. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Name: 3,4-Dibromoaniline).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Name: 3,4-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary