Author: Jessica.F

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones was written by Shen, Chaoren;Li, Wanfang;Yin, Hongfei;Spannenberg, Anke;Skrydstrup, Troels;Wu, Xiao-Feng. And the article was included in Advanced Synthesis & Catalysis in 2016.Computed Properties of C7H6BrF This article mentions the following:

An unexpected palladium-catalyzed carbonylative synthesis of 2,3-disubstituted chromones I (R = 7-Me, 6-Cl, 6-CHF₂, etc.; R¹ = 2-Me, 4-MeO, 2,4-Cl₂, etc.; R² = 4-ClC₆H₄, 4-MeC₆H₄, CH₂C₆H₅, etc.) has been developed. Starting from 2-bromofluorobenzenes R⁴2-BrFC₆H₃ (R⁴ = 4-Me, 5-Me, 6-F, etc.) and ketones R²(O)CCH₂C₆H₄R¹, the corresponding chromones I were produced in good yields. By control experiments, this transformation was found to proceed through a sequential carbonylation/Claisen-Hasse rearrangement/intramol. nucleophilic aromatic substitution approach (SNAr). More specifically, the reaction sequence started with a palladium-catalyzed carbonylation of the ketone with o-bromofluorobenzene to give the vinyl benzoates, which subsequently transformed into 1,3-diketones via a Claisen-Hasse rearrangement. The final products were produced after an intramol. SNAr reaction of the in situ formed 1,3-diketone. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Computed Properties of C7H6BrF).

3-Bromo-4-fluorotoluene (cas: 452-62-0) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Computed Properties of C7H6BrF

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

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

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

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

Hypervalent Chalcogenonium…π Bonding Catalysis was written by Zhang, Qingyu;Chan, Yung-Yin;Zhang, Muyin;Yeung, Ying-Yeung;Ke, Zhihai. And the article was included in Angewandte Chemie, International Edition in 2022.SDS of cas: 128-08-5 This article mentions the following:

A proof-of-concept study of hypervalent chalcogenonium…π bonding catalysis was performed. A new catalytic strategy using 1,2-oxaselenolium salts as chalcogen bond donors and alkenes as chalcogen bond acceptors is described. The feasibility of this concept is demonstrated by the use of trisubstituted selenonium salts in the metal-free catalytic hydrofunctionalization and polymerization of alkenes via unconventional seleniranium ion-like intermediates. The results indicate that counter anions have a significant effect on the catalysis based on hypervalent chalcogenonium…π bonding interactions. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5SDS of cas: 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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 principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.SDS of cas: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

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

Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation and Benzylation at the Benzene Core of 2-Phenylpyrroles was written by Wahl, Johannes M.;Poethig, Alexander;Bach, Thorsten. And the article was included in Organic Letters in 2016.Reference of 954-81-4 This article mentions the following:

Pyrrole has been employed for the first time as a directing group in the Pd(II)-catalyzed ortho-functionalization of C(sp²)-H bonds. A variety of substituted 2-phenylpyrroles were successfully methylated, alkylated, or benzylated in the ortho-position of the benzene ring, yielding the resp. 2-substituted pyrrol-2-yl benzenes (36 examples, 51-93% yield). Neither additives nor addnl. ligands were required to perform the reaction, which was routinely conducted with PdBr₂ as the catalyst and Li₂CO₃ as the base. Mechanistically, there is evidence that precoordination of palladium to the pyrrole enables the regioselective ortho-attack. 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. 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.Reference of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Non-ionic thiolated cyclodextrins – the next generation was written by Moghadam, Ali;Ijaz, Muhammad;Asim, Mulazim Hussain;Mahmood, Arshad;Jelkmann, Max;Matuszczak, Barbara;Bernkop-Schnuerch, Andreas. And the article was included in International Journal of Nanomedicine in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

The current study was aimed at developing a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Thiolated beta CD (β-CD) was prepared through bromine substitution of its hydroxyl groups followed by replacement to thiol groups using thiourea. The thiolated β-CD was characterized in vitro via dissolution studies, cytotoxicity studies, mucoadhesion studies on freshly excised porcine intestinal mucosa, and inclusion complex formation with miconazole nitrate. Thiolated β-CDs namely β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ displayed 558.66 ± 78 and 1,163.45 ± 96 μmol thiol groups per g of polymer, resp. Stability constant (Kc) of 190 M^-1 confirmed the inclusion complex formation of miconazole nitrate with β-CD-SH. Inclusion complexes of β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ resulted in 157- and 257-fold increased solubility of miconazole nitrate, resp. In addition, more than 80% of thiol groups were stable even after 6 h at pH 5. Both β-CD-SH compounds showed at least 1.3-fold improved solubility in water. In contrast to cationic thiolated CDs of the first generation, both thiomers showed no significant cytotoxicity. The mucoadhesive properties of the new thiolated CDs were 39.73- and 46.37-fold improved, resp. These results indicate that β-CD-SH might provide a new favorable tool for delivery of poorly soluble drugs providing a prolonged residence time on mucosal surfaces. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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. 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.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary