Tag: 200-300

A Multivalent Approach to the Design and Discovery of Orally Efficacious 5-HT₄ Receptor Agonists was written by McKinnell, R. Murray;Armstrong, Scott R.;Beattie, David T.;Choi, Seok-Ki;Fatheree, Paul R.;Gendron, Roland A. L.;Goldblum, Adam;Humphrey, Patrick P.;Long, Daniel D.;Marquess, Daniel G.;Shaw, J. P.;Smith, Jacqueline A. M.;Turner, S. Derek;Vickery, Ross G.. And the article was included in Journal of Medicinal Chemistry in 2009.Product Details of 954-81-4 This article mentions the following:

5-HT₄ receptor agonists such as tegaserod have demonstrated efficacy in the treatment of constipation predominant irritable bowel syndrome (IBS-C), a highly prevalent disorder characterized by chronic constipation and impairment of intestinal propulsion, abdominal bloating, and pain. The 5-HT₄ receptor binding site can accommodate functionally and sterically diverse groups attached to the amine nitrogen atom of common ligands, occupying what may be termed a “secondary” binding site. Using a multivalent approach to lead discovery, the effects of varying the position and nature of the secondary binding group were investigated as a strategy to achieve the desired 5-HT₄ agonist pharmacol. profile. It was shown that the ability of amine-based secondary binding groups to impart exceptional gains in the binding affinity, selectivity, and functional potency of 5-HT₄ agonists. Optimization of the leads generated by this approach afforded compound I, a selective, orally efficacious 5-HT₄ agonist for the potential treatment of gastrointestinal motility-related disorders. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Product Details of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Product Details of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Isoform-Selective and Stereoselective Inhibition of Hypoxia Inducible Factor-2 was written by Scheuermann, Thomas H.;Stroud, Daniel;Sleet, Christopher E.;Bayeh, Liela;Shokri, Cameron;Wang, Hanzhi;Caldwell, Charles G.;Longgood, Jamie;MacMillan, John B.;Bruick, Richard K.;Gardner, Kevin H.;Tambar, Uttam K.. And the article was included in Journal of Medicinal Chemistry in 2015.Name: Methyl 3-bromo-5-fluorobenzoate This article mentions the following:

Hypoxia inducible factor (HIF) transcription factors reside at the center of signaling pathways used by mammalian cells to sense and respond to low oxygen levels. While essential to maintain oxygen homeostasis, misregulation of HIF protein activity correlates with tumor development and metastasis. To provide artificial routes to target misregulated HIF activity, the authors identified small mol. antagonists of the HIF-2 transcription factor that bind an internal cavity within the C-terminal PAS domain of the HIF-2浼?subunit. Here the authors describe a new class of chiral small mol. ligands that provide the highest affinity binding, the most effective, isoform-selective inhibition of HIF-2 in cells, and trigger the largest protein conformation changes reported to date. The current results further illuminate the mol. mechanism of HIF-2 antagonism and suggest addnl. routes to develop higher affinity and potency HIF-2 antagonists. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8Name: Methyl 3-bromo-5-fluorobenzoate).

Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: Methyl 3-bromo-5-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols was written by Chalal, Malik;Vervandier-Fasseur, Dominique;Meunier, Philippe;Cattey, Helene;Hierso, Jean-Cyrille. And the article was included in Tetrahedron in 2012.Name: 5-Bromo-2-(hydroxymethyl)phenol This article mentions the following:

Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives, e.g., I. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Addnl., a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reaction steps, the waste toxicity, and the use of costly reagents. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4Name: 5-Bromo-2-(hydroxymethyl)phenol).

5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: 5-Bromo-2-(hydroxymethyl)phenol

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones was written by Jia, Feng-Cheng;Xu, Cheng;Cai, Qun;Wu, An-Xin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.SDS of cas: 653-92-9 This article mentions the following:

A highly efficient three-component domino protocol has been developed for the synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones from simple and readily available o-halogenated benzohydrazides, aldehydes and nitriles. This domino process involves sequential selective condensation, copper-catalyzed intermol. C-arylation and bicyclization. Notably, the use of ligands and anaerobic conditions can be avoided in this reaction. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9SDS of cas: 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. SDS of cas: 653-92-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of phthalonitriles using a palladium catalyst was written by Iqbal, Zafar;Lyubimtsev, Alexey;Hanack, Michael. And the article was included in Synlett in 2008.Formula: C6H5Br2N This article mentions the following:

An easy synthetic method to obtain phthalonitriles from o-dibromobenzenes under mild conditions in high yields using Zn(CN)₂ and a catalytic amount of tris(dibenzylideneacetone)dipalladium and 1,1′-bis(diphenylphosphino)ferrocene is described. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Formula: C6H5Br2N).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Formula: C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A highly practical and convenient halogenation of fused heterocyclic N-oxides was written by Wang, Dong;Wang, Yuxi;Zhao, Junjie;Li, Linna;Miao, Longfei;Wang, Dong;Sun, Hua;Yu, Peng. And the article was included in Tetrahedron in 2016.Synthetic Route of C12H7BrN2 This article mentions the following:

A novel, simple and practical method for the regioselective halogenation of fused heterocyclic N-oxides was developed. It employs Vilsmeier reagent, generated in situ by POX₃ and DMF, as both the activating agent and the nucleophilic halide source. The method is amenable across a broad range of substrates, including quinolines, isoquinolines and the diazine N-oxides, possessing a variety of substitution patterns. Furthermore, all of the reagents associated are cheap and easy to obtain. The potential extension of this method to a one-pot oxidation/halogenation sequence that obviates the need for isolation of the N-oxide intermediates is also presented. In the experiment, the researchers used many compounds, for example, 2-Bromo-1,10-phenanthroline (cas: 22426-14-8Synthetic Route of C12H7BrN2).

2-Bromo-1,10-phenanthroline (cas: 22426-14-8) 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. 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.Synthetic Route of C12H7BrN2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Platinum and Palladium Complexes Containing Cationic Ligands as Catalysts for Arene H/D Exchange and Oxidation was written by Emmert, Marion H.;Gary, J. Brannon;Villalobos, Janette M.;Sanford, Melanie S.. And the article was included in Angewandte Chemie, International Edition in 2010.Reference of 35065-86-2 This article mentions the following:

Palladium(II) and platinum(II) complexes of pyridinium-substituted bipyridine ligands I (R = Ph, 4-tBu-C₆H₄) are highly active and stable catalysts for H/D exchange and acetoxylation of aromatic C-H bonds (TONs up to 3200, TOFs up to 0.1 s-1). The regioselectivity of the deuteration and acetoxylation is studied and compared to traditional catalysts. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Reference of 35065-86-2).

3-Bromophenyl acetate (cas: 35065-86-2) 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. 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.Reference of 35065-86-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters was written by Pokorny, Jan;Olejnikova, Denisa;Frydrych, Ivo;Liskova, Barbora;Gurska, Sona;Benicka, Sandra;Sarek, Jan;Kotulova, Jana;Hajduch, Marian;Dzubak, Petr;Urban, Milan. And the article was included in European Journal of Medicinal Chemistry in 2021.Synthetic Route of C8H7BrO2 This article mentions the following:

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Four compounds had IC₅₀ below 5娓璵ol/L; I and II were selected for studies of the mechanism of action. Cell cycle anal. revealed an increase in the number of apoptotic cells at 5 x IC₅₀ concentration, where activation of irreversible changes leading to cell death can be expected. Both I and II led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 x IC₅₀ and almost complete inhibition at 5 x IC₅₀. Interestingly, compound II at 5 x IC₅₀ caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds I and II trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacol. parameters of derivative I were superior to II, therefore I was the finally selected candidate for the development of anticancer drug. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Synthetic Route of C8H7BrO2).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. 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.Synthetic Route of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic and Structure/Activity Studies on Acid-Substituted 2-Arylphenols: Discovery of 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic Acid, a High-Affinity Leukotriene B₄ Receptor Antagonist was written by Sawyer, J. Scott;Bach, Nicholas J.;Baker, S. Richard;Baldwin, Ronald F.;Borromeo, Peter S.;Cockerham, Sandra L.;Fleisch, Jerome H.;Floreancig, Paul;Froelich, Larry L.. And the article was included in Journal of Medicinal Chemistry in 1995.Category: bromides-buliding-blocks This article mentions the following:

Structural derivatives of LY255283 have been studied as receptor antagonists of leukotriene B₄. Substitution of the 2-hydroxyacetophenone subunit of 1-[5-Ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]phenyl]ethanone (LY255283) with a 2-arylphenol group provided entry into several new series that feature various mono- and diacidic core functionality. These new analogs, the subject of a broad structure-activity investigation, displayed significantly increased in vitro and in vivo activity as receptor antagonists of LTB₄. A series of diaryl ether carboxylic acids demonstrated especially interesting activity and led to the discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid (LY293111), a 2-arylphenol-substituted diaryl ether carboxylic acid which displayed potent binding to human neutrophils (IC₅₀ = 17 鍗?4.6 nM) and guinea pig lung membranes (IC₅₀ = 6.6 鍗?0.71 nM), inhibition of LTB₄-induced expression of the CD11b/CD18 receptor on human neutrophils (IC₅₀ = 3.3 鍗?0.81 nM), and inhibition of LTB₄-induced contraction of guinea pig lung parenchyma (pK_B = 8.7 鍗?0.16). 801Vivo, LY293111 demonstrated potent activity in inhibiting LTB₄-induced airway obstruction in the guinea pig when dosed by the oral (ED₅₀ = 0.40 mg/kg) or i.v. (ED₅₀ = 0.014 mg/kg) routes. A specific LTB₄ receptor antagonist, LY293111 had little effect on inhibiting contractions of guinea pig lung parenchyma induced by leukotriene D₄ (LTD₄), histamine, carbachol, or U46619. LY293111 was chosen as a clin. candidate and is currently in phase I studies for a variety of inflammatory diseases. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Category: bromides-buliding-blocks).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Oxygen Donor-Mediated Equilibration of Diastereomeric Alkene-Palladium(II) Intermediates in Enantioselective Desymmetrizing Heck Cyclizations was written by Machotta, Axel B.;Straub, Bernd F.;Oestreich, Martin. And the article was included in Journal of the American Chemical Society in 2007.Application of 2178-24-7 This article mentions the following:

This investigation examines the origin of enantioselection in the desymmetrization of an acyclic prochiral Heck cyclization precursor. High asym. induction (97-98% ee) is attributed to a temporary interaction of a Lewis basic oxygen donor with weakly Lewis acidic palladium(II). A series of control experiments combined with quantum-chem. model calculations provided sound evidence for a mechanism involving oxygen donor-mediated, rapid equilibration of diastereomeric alkene-palladium(II) complexes prior to the selectivity-determining ring-closing event, a Curtin-Hammett scenario. Our study also highlights the importance of the cationic pathway (triflate counter anions vs. halido ligand) and alkene stereochem. (E vs. Z) in asym. Heck reactions. In the experiment, the researchers used many compounds, for example, Ethyl (2-bromophenyl)acetate (cas: 2178-24-7Application of 2178-24-7).

Ethyl (2-bromophenyl)acetate (cas: 2178-24-7) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 2178-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary