Tag: 200-300

Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine N-Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains¹ was written by Lu, Jian;Bart, Aaron G.;Wu, Qian;Criscione, Kevin R.;McLeish, Michael J.;Scott, Emily E.;Grunewald, Gary L.. And the article was included in Journal of Medicinal Chemistry in 2020.Reference of 954-81-4 This article mentions the following:

The enzyme phenylethanolamine N-methyltransferase (PNMT, EC 2.1.1.28) catalyzes the final step in the biosynthesis of epinephrine and is a potential drug target, primarily for the control of hypertension. Unfortunately, many potent PNMT inhibitors also possess significant affinity for the a₂-adrenoceptor, which complicates the interpretation of their pharmacol. A bisubstrate analog approach offers the potential for development of highly selective inhibitors of PNMT. This paper documents the design, synthesis, and evaluation of such analogs, several of which were found to possess human PNMT (hPNMT) inhibitory potency <5 nM vs. AdoMet. Site-directed mutagenesis studies were consistent with bisubstrate binding. Two of these compounds (19 and 29) were co-crystallized with hPNMT and the resulting structures revealed both compounds bound as predicted, simultaneously occupying both substrate binding domains. This bisubstrate inhibitor approach has resulted in one of the most potent (20) and selective (vs the a_2-adrenoceptor) inhibitors of hPNMT yet reported. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Reference of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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). 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 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fluoroaryl analogs of sulforaphane – A group of compounds of anticancer and antimicrobial activity was written by Cierpial, Tomasz;Kielbasinski, Piotr;Kwiatkowska, Malgorzata;Lyzwa, Piotr;Lubelska, Katarzyna;Kuran, Dominika;Dabrowska, Aleksandra;Kruszewska, Hanna;Mielczarek, Lidia;Chilmonczyk, Zdzislaw;Wiktorska, Katarzyna. And the article was included in Bioorganic Chemistry in 2020.Formula: C13H14BrNO2 This article mentions the following:

A series of new sulforaphane analogs bearing various (poly)fluoroaryl substituents bonded to the sulfinyl sulfur atom in place of the original Me group and having different number of methylene groups in the central alkyl chain were synthesized and fully characterized. The new compounds were tested in vitro for their anticancer, antibacterial, antifungal and antiviral properties. Some of them demonstrated a much higher anticancer activity against selected lines of cancer: skin (MALME-3M), colon (HT-29) and breast (MCF7 and MDA-MB-231) cells than that exhibited by native sulforaphane (SFN). Related lines of untransformed (normal) cells, taken from the same organs as the cancer ones, i.e. MALME3, CRL-1790 and MCF10, resp., were checked, which allowed for the determination of the selectivity indexes (SI). In certain cases, the latter exceeded 3.2. Concerning the antibacterial activity, gram-pos. bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) were susceptible to some newly synthesized SFN analogs, while the selected probiotic strains were from 10 to 100 fold more resistant to them, which gives a possibility of protection of symbiont strains during a potential therapy with such compounds The antifungal activity of the new compounds possessing the fluorophenyl substituent was found to be higher than the activity of the parent SFN. In turn, most of the new compounds showed generally no anti-HIV activity. The influence of the particular structural differences in the new mols., analogs of SFN, on their biol. activity is discussed. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Formula: 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. 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.Formula: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

pK_a Values and Geometries of Secondary and Tertiary Amines Complexed to Boronic Acids-Implications for Sensor Design was written by Wiskur, Sheryl L.;Lavigne, John J.;Ait-Haddou, Hassan;Lynch, Vincent;Chiu, Yu Hung;Canary, James W.;Anslyn, Eric V.. And the article was included in Organic Letters in 2001.Application of 166821-88-1 This article mentions the following:

The pK_a values and the geometries of secondary and tertiary amines adjacent to boronic acids (e.g. 2-(PhCH₂NRCH₂)C₆H₄B(OH)₂; R = H, Me) were determined using potentiometric and ¹¹B NMR titrations The studies showed that the secondary ammonium ion has a pK_a similar to that of the tertiary ammonium species, which gives tetrahedral B centers at pH values â‰?.5. Therefore, secondary amines as well as tertiary amines, when placed proximal to B centers, can be used to create tetrahedral boronic acids at neutral pH for diol complexation. The mol. structure of 2,6-(2-(2-((HO)₂B)C₆H₄CH₂NHCH₂)-4-pyrimidinyl)₂pyridine was determined by x-ray crystallog. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Application of 166821-88-1).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 166821-88-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Halogen derivatives of quinone. Part II was written by Ling, Arthur R.;Baker, Julian L.. And the article was included in Journal of the Chemical Society, Transactions in 1892.COA of Formula: C6H3BrClNO3 This article mentions the following:

The behavior of chlorotribromoquinone and trichlorobromoquinone toward alkalis was investigated. Chlorotribromoquinone, when heated with potassium hydroxide solution, yields chlorobromanilic acid, whereas the action of potassium hydroxide on quinone produces potassium chlorobromanilate. The action of potassium hydroxide and sodium hydroxide on quinone leads to the formation of a compound consisting of chlorobromanilate and bromanilate. Trichlorobromoquinone, when treated with potassium hydroxide, produces a uniform product consisting of chloranilate and chlorobromanilate, contrary to previous experiments in which chlorobromanilic acid was obtained. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2COA of Formula: C6H3BrClNO3).

4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. COA of Formula: C6H3BrClNO3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Cytotoxic and antivascular 1-methyl-4-(3-fluoro-4-methoxyphenyl)-5-(halophenyl)-imidazoles was written by Biersack, Bernhard;Muthukumar, Yazh;Schobert, Rainer;Sasse, Florenz. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Application In Synthesis of 3,5-Dibromo-4-methoxybenzaldehyde This article mentions the following:

A series of 1-methyl-4,5-diphenylimidazoles 6 with various patterns of m-halogen substitution at the 5-Ph ring were tested for cytotoxicity in cancer and nonmalignant cell lines and for their capacity to prevent tube formation in HUVEC cultures. Unlike the monofluoro and difluoro derivatives 6a and 6e, the monobromo and diiodo analogs 6c and 6h were strongly cytotoxic and inhibited the polymerization of tubulin and the tube formation by HUVEC. The dibromo derivative 6g displayed a unique selectivity for KB-3-1 cervix and PC-3 prostate cancer cells. It also inhibited the tube formation by HUVEC and the polymerization of tubulin which is indicative of its potential antiangiogenic activity in solid tumors. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Application In Synthesis of 3,5-Dibromo-4-methoxybenzaldehyde).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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. 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.Application In Synthesis of 3,5-Dibromo-4-methoxybenzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The discovery of long-acting saligenin β₂ adrenergic receptor agonists incorporating a urea group was written by Procopiou, Panayiotis A.;Barrett, Victoria J.;Ford, Alison J.;Looker, Brian E.;Lunniss, Gillian E.;Needham, Deborah;Smith, Claire E.;Somers, Graham. And the article was included in Bioorganic & Medicinal Chemistry in 2011.Synthetic Route of C7H7BrN2O2 This article mentions the following:

A series of novel, potent and selective human β₂ adrenoceptor agonists incorporating a urea moiety on the terminal right-hand side Ph ring of (R)-salmeterol is presented. Urea 9j (I) had long duration of action in vitro on guinea pig trachea, and also in vivo similar to that of salmeterol. It had lower oral absorption and bioavailability than salmeterol in both rat and dog. It had a turnover ratio similar to salmeterol, with no evidence for formation of any aniline metabolites in human liver microsomes and hepatocytes. However no crystalline salts suitable for inhaled delivery were identified. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7Synthetic Route of C7H7BrN2O2).

2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7) 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.Synthetic Route of C7H7BrN2O2

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Bromide – Wikipedia,
bromide – Wiktionary

Arylation of aryllithiums with S-arylphenothiazinium ions for biaryl synthesis was written by Morofuji, Tatsuya;Yoshida, Tatsuki;Tsutsumi, Ryosuke;Yamanaka, Masahiro;Kano, Naokazu. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.SDS of cas: 162258-89-1 This article mentions the following:

Herein, arylation of aryllithiums ArLi (Ar = Ph, 4-MeOC₆H₄, 1-naphthyl, etc.) with S-arylphenothiazinium ions I (R¹ = H, 4-Br, 4-t-Bu, etc.) through selective ligand coupling of intermediary sulfuranes is reported. Various unsym. biaryls II (R¹ = H, 4-Br, 4-SMe, etc.; R² = H, 4-Cl, 4-I, etc.) could be obtained without transition-metal catalysis. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1SDS of cas: 162258-89-1).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.SDS of cas: 162258-89-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

N-alkoxy-N-acylnitrenium ions in intramolecular aromatic addition reactions was written by Glover, Stephen A.;Goosen, Andre;McCleland, Cedric W.;Schoonraad, Johan L.. And the article was included in Tetrahedron in 1987.Electric Literature of C10H13BrO This article mentions the following:

N-Alkoxy-N-acylnitrenium ions are generated by treating N-alkoxy-N-chloroamides with Ag⁺ ions in ethereal solvents. These intermediates readily cyclize onto aromatic nuclei on alkoxy side chains to give benzoxazines and benzoxazepines and on acyl side chains to give γ-, δ-, and ε-benzolactams. E.g., treating Ph(CH₂)₃ONClBz in Et₂O with AgBF₄ gave 50% benzoxazepine I. Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side chain aromatic rings. The yields and regioselectivities of these reactions are ascribed to different transition structures for cyclization onto the acyl and alkoxy side chains, which involve an exo- and endocyclic N⁺-O π-bond, resp. Evidence for this exceptionally high π-bond character is obtained from MNDO calculations, which predict a π-bond order of 0.9 and a rotational barrier of 29.7 kcal mol^-1. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. 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.Electric Literature of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Preparation of aromatic sulfonyl halides was written by Jenkins, F. E.;Hambly, A. N.. And the article was included in Australian Journal of Chemistry in 1953.Recommanded Product: 454-65-9 This article mentions the following:

The following RC₆H₄SO₂Cl are prepared by chlorination of the RSO₂H, which are obtained by the modified Gattermann procedure (addition of the diazonium sulfate of the appropriate amine to a suspension of Cu powder in dilute H₂SO₄ saturated with SO₂) (R, % yield given): m-Me, 50, b_0.3 77-8° (sulfonamide, m. 108.5-9.5°); ο-MeO, 51; m-Cl, 50; m-Br, 54. Refluxing the RC₆H₄SO₂Cl with excess of a saturated aqueous solution of KF gave RC₆H₄SO₂F: m-Me, 85, b_1.4 78.5-79°, n²⁵_D 1.4909; ο-MeO, 42, m. 39-40°; p-AcNH (I), 47, m. 176°; m-Cl, 63, b_0.8 69-70°, n²⁵_D 1.5114; m-Br, 63, b_1.0 90°, n²⁵_D 1.5358; p-O₂N (II), 65, m. 77.5-8.5°. I is best prepared in aqueous dioxane. Reduction of II with Sn and HCl gives p-H₂NC₆H₄SO₂F (45%), m. 72-3°, converted into I by Ac₂O in AcOH. In the experiment, the researchers used many compounds, for example, 3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9Recommanded Product: 454-65-9).

3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. 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.Recommanded Product: 454-65-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Enantioselective Vinylogous Mannich-Type Reactions to Construct CF₃S-Containing Stereocenters Catalysed by Chiral Quaternary Phosphonium Salts was written by Xu, Lijun;Yu, Longhui;Liu, Jun;Wang, Hongyu;Zheng, Changwu;Zhao, Gang. And the article was included in Advanced Synthesis & Catalysis in 2020.Name: 1-(Bromomethyl)-4-fluoro-2-nitrobenzene This article mentions the following:

A series of benzyl trifluoromethyl sulfides bearing a nitro group was utilized as CF₃S-containing building blocks R-2-O₂NC₆H₃CH₂SCF₂X (R = H, 4-F, 5-Cl, 4-Br; X = F, CF₃) to construct chiral CF₃S-containing mols. I (R¹ = naphthalen-1-yl, thiophen-2-yl, 4-methylphenyl, etc.) via enantioselective vinylogous Mannich-type reactions. In such reactions, high yields and enantioselectivities were obtained using chiral quaternary phosphonium salts II (R² = Ph, 3-nitrophenyl) derived from amino acids. Moreover, a chiral cyclic urea bearing the CF₃S moiety III was obtained from further transformation of the product I (R = H; R¹ = Ph; X = F). In the experiment, the researchers used many compounds, for example, 1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0Name: 1-(Bromomethyl)-4-fluoro-2-nitrobenzene).

1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0) 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). 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.Name: 1-(Bromomethyl)-4-fluoro-2-nitrobenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary