Month: January 2023

Regioselective Bromination of Fused Heterocyclic N-Oxides was written by Wengryniuk, Sarah E.;Weickgenannt, Andreas;Reiher, Christopher;Strotman, Neil A.;Chen, Ke;Eastgate, Martin D.;Baran, Phil S.. And the article was included in Organic Letters in 2013.Application In Synthesis of 2-Bromo-1,10-phenanthroline This article mentions the following:

A mild method for the regioselective C2-bromination of fused azine N-oxides is presented, employing tosic anhydride as the activator and tetra-n-butylammonium bromide as the nucleophilic bromide source. The C2-brominated compounds, e.g. I [X = H, 4-OMe, 6-OMe, etc.], are produced in moderate to excellent yields and with excellent regioselectivity in most cases. The potential extension of this method to other halogens, effecting C2-chlorination with Ts₂O/TBACl is also presented. Finally, this method could be incorporated into a viable one-pot oxidation/bromination process, using methyltrioxorhenium/urea hydropgen peroxide as the oxidant. In the experiment, the researchers used many compounds, for example, 2-Bromo-1,10-phenanthroline (cas: 22426-14-8Application In Synthesis of 2-Bromo-1,10-phenanthroline).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists was written by Nomura, Sayaka;Endo-Umeda, Kaori;Makishima, Makoto;Hashimoto, Yuichi;Ishikawa, Minoru. And the article was included in ChemMedChem in 2016.Reference of 57293-19-3 This article mentions the following:

Liver X receptor (LXR) agonists are candidates for the treatment of atherosclerosis via induction of ABCA1 (ATP-binding cassette A1) gene expression, which contributes to reverse cholesterol transport (RCT) and to cholesterol efflux from the liver and intestine. However, LXR agonists also induce genes involved in lipogenesis, such as SREBP-1c (sterol regulatory binding element protein 1c) and FAS (fatty acid synthase), thereby causing an undesirable increase in plasma and hepatic triglyceride (TG) levels. Recent studies indicate that LXRα contributes to lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand-binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study the authors identified a tetrachlorophthalimide analog as an LXRβ-selective agonist. Structural development led to (E)-4,5,6,7-tetrachloro-2-(2-styrylphenyl)isoindoline-1,3-dione (I), which shows potent and selective LXRβ agonistic activity in reporter gene assays. In binding assays, compound I bound to LXRβ preferentially over LXRα. It also induced the expression of ABCA1 mRNA but not SREBP-1c mRNA in cells. Compound I appears to be a promising lead compound for therapeutic agents to treat atherosclerosis without the side effects induced by LXRα/β dual agonists. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Reference of 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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. 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.Reference of 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Friedel-Crafts reactions of long-chain compounds substituted by a polar group was written by Matsuda, Sumio. And the article was included in Kenkyu Hokoku – Asahi Garasu Kogyo Gijutsu Shoreikai in 1973.SDS of cas: 4457-67-4 This article mentions the following:

Friedel-Crafts alkylation of C6H6 with 1-methoxy-2-, 1-methoxy-5-, and 1-methoxy-7-chlorooctane in the presence of AlCl3 gave 1-methoxy-n-phenyloctanes (n = 3-7) with various isomer compositions Alkylation at the C atoms near the MeO group was retarded by its electron withdrawing inductive effect. The inductive effects were also transmitted through the chain. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4SDS of cas: 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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 principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.SDS of cas: 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Acid-free fabrication of polyaryletherketone membranes was written by Aristizabal, Sandra L.;Upadhyaya, Lakshmeesha;Falca, Gheorghe;Gebreyohannes, Abaynesh Yihdego;Aijaz, Mohammed Omer;Karim, Mohammad Rezaul;Nunes, Suzana P.. And the article was included in Journal of Membrane Science in 2022.Related Products of 128-08-5 This article mentions the following:

Polyaryletherketones (PAEKs) are a class of ultrahigh performance polymers with outstanding temperature and chem. resistance. Poly(ether ketone ketone) copolymer (Kepstan) and poly(ether ether ketone) (PEEK) display intrinsic insolubility in nearly all organic solvents. The primary issue for the application of these polymers is their processability which requires a high temperature/pressure-based technique, or the use of harsh and corrosive solvents, like methanesulfonic and sulfuric acid, resulting in sulfonation of the polymer backbone that adversely might affect their chem. stability. In this work, we propose a method to prepare porous Kepstan and PEEK membranes using N-methyl-2-pyrrolidone (NMP) as solvent at room temperature It consisted of a modification-regeneration strategy to turn com. semi-crystalline Kepstan and PEEK into dithiolane soluble derivatives that allow the fabrication of hollow fiber, flat-sheet, and electrospun nanofibers. The resulting membranes are then regenerated to the solvent-resistant materials. The novel Kepstan and PEEK hollow fibers exhibited a N,N-dimethylformamide (DMF) permeance of 2.21 and 2.05 L m^-2 h^-2 bar^-1, with more than 90% rejection of crystal violet (408 g mol^-1) and methyl orange (327 g mol^-1), resp. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Related Products of 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Related Products of 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

N¹,N¹-Dimethyl-N³-(3-(trifluoromethyl)phenethyl)propane-1,3-diamine, a new lead for the treatment of human African trypanosomiasis was written by Pham, Ngoc B.;Deydier, Sophie;Labaied, Mehdi;Monnerat, Severine;Stuart, Kenneth;Quinn, Ronald J.. And the article was included in European Journal of Medicinal Chemistry in 2014.Application of 108940-96-1 This article mentions the following:

The natural product, convolutamine I, has anti-trypanosomal activity however it has a high mol. weight of 473 due to a presence of 3 bromine atoms. The synthesis of the natural product convolutamine I together with its analogs are presented. A SAR study against Trypanosoma brucei brucei led to compounds with improved physico-chem. properties: lower mol. weight and lower log P while maintaining potency (with a slight 2-fold improvement). In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Application of 108940-96-1).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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. 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 108940-96-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Novel CDKs inhibitors for the treatment of solid tumour by simultaneously regulating the cell cycle and transcription control was written by Wang, Xin;Deng, Kaiyuan;Wang, Cheng;Li, Yao;Wang, Tianqi;Huang, Zhi;Ma, Yakun;Sun, Peiqing;Shi, Yi;Yang, Shengyong;Fan, Yan;Xiang, Rong. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2020.Related Products of 954-81-4 This article mentions the following:

A novel series of cyclin-dependent kinases (CDKs) inhibitors, which play critical roles in the cell cycle control and regulation of cell transcription, were synthesized. A systematic study of enzymic and cellular assays led to the identification of compound with a nanomolar potency against CDK4 and CDK9 and potent antiproliferative activities against a panel of tumor cell lines. could induce cell cycle arrest and cell apoptosis in cancer cell lines. dose-dependently inhibits signalling pathways downstream of CDKs in cancer cells. In vivo antitumor activity assays, oral administration of led to significant tumor regression in mouse model without obvious toxicity. Superior anti-cancer efficacy in vitro and in vivo of demonstrated combined depletion of cell cycle and transcriptional CDK all contributed to antitumor activity. Taken together, concomitant inhibition of cell cycle and transcriptional CDK activities provided valuable guide for further structural optimization. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Related Products of 954-81-4).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Novel Multidrug Resistance Reversal Agents was written by Berger, Dan;Citarella, Ron;Dutia, Minu;Greenberger, Lee;Hallett, William;Paul, Rolf;Powell, Dennis. And the article was included in Journal of Medicinal Chemistry in 1999.Quality Control of 3-(Bromomethyl)benzoic acid This article mentions the following:

A series of 59 α-aryl-α-thioether-alkyl, -alkanenitrile, and -alkanecarboxylic acid Me ester tetrahydroisoquinoline and isoindoline derivatives I [R¹-R⁴ = H, F, Cl, OH, OCF₃, OMe, OBn, OTBDMS, OCH₂CH₂Cl, OCH₂CH₂Im (Im = imidazole), OCH₂CH₂NMe₂, OCH₂O; R⁵ = 4-MeC₆H₄, cyclohexyl; R⁶ = CN, CO₂Me, H, Et; R⁷ = H, Me, 3,4-(MeO)₂C₆H₃; R⁸ = H, OMe; n = 2-6, 8, 11; m = 1,2] were synthesized and evaluated as multidrug resistance (MDR) reversal agents. The compounds were tested on S1-B1-20 human colon carcinoma cells selected for resistance to bisantrene. Both the cytotoxicity of the reversal agents and their ability to resensitize the cells to bisantrene were determined All but two of these compounds were more effective MDR reversal agents in vitro than verapamil (VRP), a calcium channel antagonist which also has been shown to possess MDR modulating activity. Several showed good activity in this assay (IC₅₀‘s < 0.5 μM), the most potent being isoindolines I [R¹-R⁴ = OMe, R⁵ = 4-MeC₆H₄, R⁶ = CN, n = 5, m = 1; R¹-R⁴ = OMe, R⁵ = C₆H₁₁, R⁶ = CN, n = 5, m = 1] and tetrahydroisoquinolines I [R¹ = OCH₂CH₂Im, R²-R⁴ = OMe, R⁵ = 4-MeC₆H₄, R⁶ = H, n = 6, m = 2; R¹-R⁴ = OMe, R⁵ = 4-MeC₆H₄, R⁶ = CN, n = 6, m = 2]. A number of compounds were evaluated in vivo against vincristine (VCR)-resistant murine P388 leukemia, as well as against human epidermoid carcinoma KB/8.5 implanted s.c. in athymic mice. The reversal agents which consistently showed the highest activity, together with low toxicity, were α-aryl-α-thiotolylalkanenitrile tetrahydroisoquinoline derivatives with electron-rich alkoxy substituents on the aromatic rings. Of the tested compounds, the most effective reversal agents for both tumor lines were tetrahydroisoquinolines I [R¹-R⁴ = OMe, R⁵ = 4-MeC₆H₄, R⁶ = CN, n = 5, m = 2] (33% increased life span at 12.5 mg/kg, 0.2 mg/kg VCR vs. VCR alone in the VCR-resistant P388 leukemia model and 59% relative tumor growth at 50 mg/kg, 8 mg/kg doxorubicin vs. doxorubicin alone in the KB/8.5 model) and I [R¹-R² and R⁴ = OMe, R³ = OCH₂CH₂Im, R⁵ = 4-MeC₆H₄, R⁶ = CN, n = 5, m = 2] (48% increased life span at 50 mg/kg, 0.2 mg/kg VCR vs. VCR alone in the VCR-resistant P388 leukemia model and 46% relative tumor growth at 25 mg/kg, 8 mg/kg doxorubicin vs. doxorubicin alone in the KB/8.5 model). The mechanism of action of these compounds is believed to involve blocking the drug efflux pump, P-glycoprotein. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Quality Control of 3-(Bromomethyl)benzoic acid).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Quality Control of 3-(Bromomethyl)benzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Concise total synthesis of aplysinellamides A and B was written by Gan, Haifeng;Huang, Yu;Feng, Weiyang;Zhu, Wentong;Guo, Kai. And the article was included in Journal of Chemical Research in 2015.Reference of 108940-96-1 This article mentions the following:

Concise and efficient total syntheses of bromotyrosine-derived metabolites aplysinellamides A (I·TFA) and B (II·TFA), isolated from Australian marine sponge Aplysinella sp., have been accomplished in seven steps. A condensation between cinnamic acid and Boc-D-lysine Me ester was applied to form the amide skeleton as a key step. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Reference of 108940-96-1).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Reference of 108940-96-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and bioevaluation of new vascular-targeting and anti-angiogenic thieno[2,3-d]pyrimidin-4(3H)-ones was written by Gold, Madeleine;Koehler, Leonhard;Lanzloth, Clarissa;Andronache, Ion;Anant, Shrikant;Dandawate, Prasad;Biersack, Bernhard;Schobert, Rainer. And the article was included in European Journal of Medicinal Chemistry in 2020.Formula: C8H6Br2O2 This article mentions the following:

A series of forty-six 5,6-annulated 2-arylthieno[2,3-d]pyrimidin-4(3H)-ones were prepared as potentially pleiotropic anticancer drugs with variance in the tubulin-binding trimethoxyphenyl motif at C-2 of a thieno[2,3-d]pyrimidine fragment, enlarged by addnl. rings of different size and substitution. By assessing their cytotoxicity against various cancer cells, their influence on the polymerization of neat tubulin and the dynamics of microtubule and F-actin cytoskeletons and their vascular-disrupting and anti-angiogenic activities in-vitro and in-vivo, structure-activity relations were identified which suggested the 3-iodo-4,5-dimethoxyphenyl substituted thienopyrimidine as a promising anticancer drug candidate for further research. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Formula: C8H6Br2O2).

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. 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.Formula: C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An improved and alternative method for the preparation of per(6-bromo-6-deoxy)cyclodextrins was written by Xue, Weihua;Zhang, Lifen. And the article was included in Synthesis in 2011.Reference of 53784-83-1 This article mentions the following:

A practical and efficient approach to the regioselective synthesis of per(6-bromo-6-deoxy)cyclodextrins is described. The method utilizes the easily accessible (chloro(phenylthio)methylene)dimethylammonium chloride (CPMA), circumventing disadvantages of earlier protocols. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Reference of 53784-83-1).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary