Month: February 2023

Rhenium(I) complexation-dissociation strategy for synthesising fluorine-18 labelled pyridine bidentate radiotracers was written by Klenner, Mitchell A.;Zhang, Bo;Ciancaleoni, Gianluca;Howard, James K.;Maynard-Casely, Helen E.;Clegg, Jack K.;Massi, Massimiliano;Fraser, Benjamin H.;Pascali, Giancarlo. And the article was included in RSC Advances in 2020.Reference of 22426-14-8 This article mentions the following:

A novel fluorine-18 method employing rhenium(I) mediation is described herein. The method was found to afford moderate to high radiochem. yields of labeled rhenium(I) complexes. Subsequent thermal dissociation of the complexes enabled the radiosynthesis of fluorine-18 labeled pyridine bidentate structures which could not be radiofluorinated hitherto. This rhenium(I) complexation-dissociation strategy was further applied to the radiosynthesis of [¹⁸F]CABS13, an Alzheimer′s disease imaging agent, alongside other 2,2′-bipyridine, 1,10-phenanthroline and 8-hydroxyquinoline labeled radiotracers. Computational modeling of the reaction mechanism suggests that the efficiency of rhenium(I) activation may be attributed to both an electron withdrawal effect by the metal center and the formation of an acyl fluoride intermediate which anchors the fluoride subsequent to nucleophilic addition In the experiment, the researchers used many compounds, for example, 2-Bromo-1,10-phenanthroline (cas: 22426-14-8Reference of 22426-14-8).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Parameters of the production of carboxin and its analogs was written by Dziedzic, Czeslaw;Eckstein, Zygmunt;Ejmocki, Zdzislaw;Miszczak, Kamila;Rusek, Dorota;Tippe, Andrzej. And the article was included in Przemysl Chemiczny in 1983.Application of 615-55-4 This article mentions the following:

Chlorinating MeCOCH₂CO₂Et (I) with SOCl₂ in C₆H₆ gave 98.1-9.9% MeCOCHClCO₂Et, which condensed with HSCH₂CH₂OH in the presence of NaHCO₃ to give the intermediate HOCH₂CH₂SCH(CO₂Et)COMe. Cyclocondensation of the latter in the presence of acid gave ester II (R = OEt), which was saponified to give 47.6-51.8% II (R = OH) (III), based on I. Treating III with SOCl₂ and then PhNH₂ and 34 other primary and secondary aromatic and heterocyclic amines yielded 21.0-98.8% II (R = substituted NH₂). The fungicidal activity of II (R = NHC₆H₄R¹; R¹ = C₁-C₅ alkoxy, F) exceeded that of II (R = NHPh). In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Application of 615-55-4).

3,4-Dibromoaniline (cas: 615-55-4) 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. 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.Application of 615-55-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen was written by Wang, Yan-en;Li, Xueyan;Chen, Hua;Zhu, Mengyuan;Li, Xiaoliu. And the article was included in Chemical Research in Chinese Universities in 2018.Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane This article mentions the following:

The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, authors reported the design and synthesis of a series of anthracene-based bisboronic acids (9a–9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) 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.Name: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Solvolysis of 2-substituted-9-(ortho-substituted phenylmethyl)fluoren-9-yltrimethylammonium ions in various solvents. The effect of steric crowding on alkene formation was written by Smith, Peter James;Pradhan, Jyotsna. And the article was included in Canadian Journal of Chemistry in 1986.Application of 83902-02-7 This article mentions the following:

The solvolytic reaction of several 9-(o-substituted phenylmethyl)fluoren-9-yltrimethylammonium salts has been investigated in several different solvents. Substitution and elimination products were found for the reactions in all the solvents studied, with the exceptions that reaction in both tert-Bu alc. and chloroform led exclusively to the alkene product. The observed rate constants for alkene formation and the percent alkene were measured and it was found that the di-o compounds reacted at a faster rate but produced less alkene than the reaction of the corresponding mono-o salts. Hydrogen-deuterium isotope effects were also determined for the various reactions. The results are discussed in terms of the reaction proceeding by way of the E1 mechanism, where steric acceleration promotes the loss of the bulky ammonium leaving group to give the carbocation intermediate. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Application of 83902-02-7).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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. 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 of 83902-02-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hybrids consisting of the pharmacophores of salmeterol and roflumilast or phthalazinone: Dual β₂-adrenoceptor agonists-PDE4 inhibitors for the treatment of COPD was written by Liu, Anqiu;Huang, Ling;Wang, Zhiren;Luo, Zonghua;Mao, Fei;Shan, Wenjun;Xie, Jiaxing;Lai, Kefang;Li, Xingshu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.SDS of cas: 954-81-4 This article mentions the following:

A novel class of dual pharmacol. bronchodilators I(n = 2, 3, 4, 5) and II(n = 1, 3, 4, 5) targeting both β₂-adrenoceptor and PDE4 was designed and synthesized by combining the pharmacophores of salmeterol and roflumilast or phthalazinone. All the compounds exhibited better β₂-adrenoceptor agonist activities (pEC₅₀ = 8.47-9.20) than the reference compound salmeterol (pEC₅₀ = 8.3) and good inhibitory activity on PDE4B2 (IC₅₀ = 0.235-1.093 μM). In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4SDS of cas: 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.SDS of cas: 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp³)-H bond functionalization was written by Mori, Keiji;Umehara, Nobuaki;Akiyama, Takahiko. And the article was included in Chemical Science in 2018.Name: 2-Bromo-4-fluorobenzylbromide This article mentions the following:

Bronsted acid-catalyzed double C(sp³)-H bond functionalization of alkyl phenethyl ether derivatives was described. In this process, a [1,5]-[1,5]-hydride shift occurred successively to afford tricyclic fused pyran derivatives in excellent chem. yields with excellent diastereoselectivities (up to >20 : 1). The key to achieve this reaction was the introduction of two Me groups at the benzylic position, which was effective in both hydride shift processes: (1) the Thorpe-Ingold effect for the first hydride shift and (2) conformational control in the second hydride shift. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Name: 2-Bromo-4-fluorobenzylbromide).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: 2-Bromo-4-fluorobenzylbromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and biological evaluation of α-1-C-4′-arylbutyl-L-arabinoiminofuranoses, a new class of α-glucosidase inhibitors was written by Natori, Yoshihiro;Sakuma, Toshihiro;Yoshimura, Yuichi;Kinami, Kyoko;Hirokami, Yuki;Sato, Kasumi;Adachi, Isao;Kato, Atsushi;Takahata, Hiroki. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Recommanded Product: 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

A series of α-1-C-4′-arylbutyl-L-arabinoiminofuranoses, e.g. I, with functional groups attached to the Ph ring, which are potential α-glycosidase inhibitors, was designed and synthesized by using a Negishi cross-coupling reaction as the key reaction. Arylbutyl derivatives, e.g. I, showed potent inhibitory activities against intestinal maltase. Among them, difluorophenylbutyl derivative I showed good inhibition activities against intestinal isomaltase and sucrase as compared to com. drugs. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Recommanded Product: 1-(3-Bromopropyl)-4-methoxybenzene).

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. 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.Recommanded Product: 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Oxidation for unsymmetrical bromo-1,10-phenanthrolines and subsequent hydroxylation, decarbonylation and chlorination reactions was written by Peng, Yu-Xin;Hu, Bin;Huang, Wei. And the article was included in Tetrahedron in 2018.Synthetic Route of C12H7BrN2 This article mentions the following:

Systematic investigation on the oxidation of unsym. bromo-phens is presented, where the reaction temperature is found to be the key parameter to generate oxidation or oxidation-bromination products. The regioselective C3-brominated compounds are produced in moderate yields in the cases of 2-bromo-phen and 4-bromo-phen. Subsequent hydroxylation and decarbonylation for bromo-phds are also studied, where a series of bromo-diazafluorenones and phen-triones have been isolated. Furthermore, various chlorination products have been obtained by treating bromo-phds or bromo-phts with excess POCl₃. 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. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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

Discovery of aminopiperidine-based Smac mimetics as IAP antagonists was written by Hennessy, Edward J.;Saeh, Jamal C.;Sha, Li;MacIntyre, Terry;Wang, Haiyun;Larsen, Nicholas A.;Aquila, Brian M.;Ferguson, Andrew D.;Laing, Naomi M.;Omer, Charles A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Electric Literature of C9H11BrO This article mentions the following:

A series of structurally unique Smac mimetics that act as antagonists of inhibitor of apoptosis proteins (IAPs) has been discovered. While most previously described Smac mimetics contain the proline ring (or a similar cyclic motif) found in Smac, a key feature of the compounds described herein is that this ring has been removed. Despite this, compounds in this series potently bind to cIAP1 and elicit the expected phenotype of cIAP1 inhibition in cancer cells. Marked selectivity for cIAP1 over XIAP is observed for these compounds, which is attributed to a slight difference in the binding groove between the two proteins and the resulting steric interactions with the inhibitors. XIAP binding can be improved by constraining the inhibitor so that these unfavorable steric interactions are minimized. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Electric Literature of C9H11BrO).

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. 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.Electric Literature of C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structural Optimizations of Thieno[3,2-b]pyrrole Derivatives for the Development of Metabolically Stable Inhibitors of Chikungunya Virus was written by Ching, Kuan-Chieh;Tran, Thi Ngoc Quy;Amrun, Siti Naqiah;Kam, Yiu-Wing;Ng, Lisa F. P.;Chai, Christina L. L.. And the article was included in Journal of Medicinal Chemistry in 2017.Synthetic Route of C5H3BrOS This article mentions the following:

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus, and there is no approved effective antiviral treatment currently available for CHIKV. We previously reported the discovery of thieno[3,2-b]pyrrole 1b that displayed good antiviral activity against CHIKV infection in vitro. However, it has a short half-life in the presence of human liver microsomes (HLMs) (T_1/2 = 2.91 min). Herein, we report further optimization studies in which potential metabolically labile sites on compound 1b were removed or modified, resulting in the identification of thieno[3,2-b]pyrrole 20 and pyrrolo[2,3-d]thiazole 23c possessing up to 17-fold increase in metabolic half-lives in HLMs and good in vivo pharmacokinetic properties. Compound 20 not only attenuated viral RNA production and displayed broad-spectrum antiviral activity against other alphaviruses and CHIKV isolates but also exhibited limited cytotoxic liability (CC₅₀ > 100 μM). These studies have identified two compounds that have the potential for further development as antiviral drugs against CHIKV infection. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2Synthetic Route of C5H3BrOS).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C5H3BrOS

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary