Tag: 200-300

Pharmacophore-Based Design of Novel Oxadiazoles as Selective Sphingosine-1-phosphate (S1P) Receptor Agonists with in vivo Efficacy was written by Quattropani, Anna;Sauer, Wolfgang H. B.;Crosignani, Stefano;Dorbais, Jerome;Gerber, Patrick;Gonzalez, Jerome;Marin, Delphine;Muzerelle, Mathilde;Beltran, Fanny;Nichols, Anthony;Georgi, Katrin;Schneider, Manfred;Vitte, Pierre-Alain;Eligert, Valerie;Novo-Perez, Laurence;Hantson, Jennifer;Nock, Sebastien;Carboni, Susanna;Soares de Souza, Adriano Luis;Arrighi, Jean-Francois;Boschert, Ursula;Bombrun, Agnes. And the article was included in ChemMedChem in 2015.Recommanded Product: 107317-58-8 This article mentions the following:

Sphingosine-1-phosphate (S1P) receptor agonists have shown promise as therapeutic agents for multiple sclerosis (MS) due to their regulatory roles within the immune, central nervous system, and cardiovascular system. Here, the design and optimization of novel [1,2,4]oxadiazole derivatives as selective S1P receptor agonists are described. The structure-activity relation exploration was carried out on the three dominant segments of the series: modification of the polar head group (P), replacement of the oxadiazole linker (L) with different five-membered heterocycles, and the use of diverse 2,2′-disubstituted biphenyl moieties as the hydrophobic tail (H). All three segments have a significant impact on potency, S1P receptor subtype selectivity, physicochem. properties, and in vitro absorption, distribution, metabolism, excretion and toxicity (ADMET) profile of the compounds From these optimization studies, a selective S1P₁ agonist, N-methyl-N-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (45), and a dual S1P_1,5 agonist, N-methyl-N-(3-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (49), emerged as frontrunners. These compounds distribute predominantly in lymph nodes and brain over plasma and induce long lasting decreases in lymphocyte count after oral administration. When evaluated head-to-head in an exptl. autoimmune encephalomyelitis mouse model, together with the marketed drug fingolimod, a pan-S1P receptor agonist, S1P_1,5 agonist 49 demonstrated comparable efficacy while S1P₁-selective agonist 45 was less potent. Compound 49 is not a prodrug, and its improved property profile should translate into a safer treatment of relapsing forms of MS. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Recommanded Product: 107317-58-8).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: 107317-58-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of compounds allied to rhododendrin was written by Kim, Ki-U. And the article was included in Yakugaku Zasshi in 1943.HPLC of Formula: 57293-19-3 This article mentions the following:

In order to exam. the pharmacol. action of compounds allied to rhododendrin, the following compounds were synthesized. 1-(p-Hydroxyphenyl)-2-propanol: p-MeOC₆H₄CH:CHMe(+ Br) 閳?MeOC₆H₄CHBrCHBrMe (+ CaO) 閳?MeOC₆H₄CH(OH)CHBrMe (+ 2.5% alkali) 閳?MeOC₆H₄CH(OH)CH(OH)Me (heating to 180鎺? 閳?MeOC₆H₄CH₂COMe (+ Na + EtOH) 閳?MeOC₆H₄CH₂CH(OH)Me (+ Grignard reagent) 閳?p-HOC₆H₄CH₂CH(OH)Me. 5-(p-Hydroxyphenyl)-2-pentanol: p-MeOC₆H₄CHO + AcOEt (+ Na) 閳?MeOC₆H₄CH:CHCO₂Et (+ H) 閳?MeOC₆H₄CH₂CH₂CO₂Et (+ Na + AmOH) 閳?MeOC₆H₄(CH₂)₃OH (+ PBr₃) 閳?MeOC₆H₄(CH₂)₃Br 閳?MeOC₆H₄(CH₂)₃CN (+ MeMgI) 閳?MeOC₆H₄(CH₂)₃COMe 閳?MeOC₆H₄(CH₂)₃CH(OH)Me 閳?HOC₆H₄(CH₂)₃CH(OH)Me. By similar methods were prepared: 6-(p-hydroxyphenyl)-2-hexanol, from p-MeOC₆H₄CHO and EtCOMe; 1-(m-hydroxyphenyl)-3-butanol, from m-MeOC₆H₄CHO and Me₂CO; 1-(4-hydroxy-3-methoxyphenyl)-3-butanol, from vanillin and Me₂CO; 1-(p-hydroxyphenyl)-3-pentanol, from p-MeOC₆H₄CHO and AcOEt; 1-(4-hydroxy-3-methylphenyl)-3-butanol from 3,4-Me(HO)C₆H₃CHO (prepared from m-MeC₆H₄OH, HCN, AlCl₃, and HCl) and Me₂CO; 1-(4-hydroxy-2-methylphenyl)-3-butanol, from 2,4-Me(HO)C₆H₃CHO and Me₂CO; and 1-(4-hydroxy-5-isopropyl-2-methylphenyl)-3-butanol, from 5,2-Me(Me₂CH)C₆H₃OH through 2,5,4-Me(Me₂CH)(HO)C₆H₂CHO. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3HPLC of Formula: 57293-19-3).

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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. HPLC of Formula: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of 浼?Amino-灏?Bromo Acid Esters with Aryl Bromides was written by Tang, Shi;Xu, Zhen-Hua;Liu, Ting;Wang, Shuo-Wen;Yu, Jian;Liu, Jian;Hong, Yu;Chen, Shi-Lu;He, Jin;Li, Jin-Heng. And the article was included in Angewandte Chemie, International Edition in 2021.Synthetic Route of C8H7BrO2 This article mentions the following:

Here an unprecedented, efficient nickel-catalyzed radical relay was reported for the remote cross-electrophile coupling of 灏?bromo-浼?benzylamino acid esters with aryl bromides via 1,4-aryl migration/arylation cascades. 灏?Bromo-浼?benzylamino acid esters were considered as unique mol. scaffolds allowing for aryl migration reactions, which were conceptually novel variants for the radical Truce-Smiles rearrangement. This reaction enabled the formation of two new C(sp3)-C(sp2) bonds using a bench-stable Ni/bipyridine/Zn system featuring a broad substrate scope and excellent diastereoselectivity, which provided an effective platform for the remote aryl group migration and arylation of amino acid esters via redox-neutral C(sp3)-C(sp2) bond cleavage. Mechanistically, this cascade reaction was accomplished by combining two powerful catalytic cycles consisting of a cross-electrophile coupling and radical 1,4-aryl migration through the generation of C(sp3)-centered radical intermediates from the homolysis of C(sp3)-Br bonds and the switching of the transient alkyl radical into a robust 浼?aminoalkyl radical. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Synthetic Route of C8H7BrO2).

3-Bromophenyl acetate (cas: 35065-86-2) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Efficient Access to Methyl-1-hydroxy-2-naphthoates and Heterocyclic Analogues was written by Podeschwa, Michael A. L.;Rossen, Kai. And the article was included in Organic Process Research & Development in 2015.Quality Control of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

We report the synthesis of Me 1-hydroxy-2-naphthoate derivatives and heterocyclic analogs using a two-step approach. This short route employs a Heck coupling of a 2-halobenzoate with Me 3-butenoate followed by a Dieckmann cyclization, yielding the 1-hydroxynaphthalene-2-carboxylic acid derivatives in the multigram scale. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Quality Control of Methyl 2-bromo-4-fluorobenzoate).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium(0) catalyzed cross coupling reactions of hindered, double activated aryl halides with organozinc reagents – the effect of copper(I) cocatalysis was written by Weichert, Andreas;Bauer, Martina;Wirsig, Petra. And the article was included in Synlett in 1996.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate This article mentions the following:

Various organozinc reagents undergo palladium(0) catalyzed Negishi-Kumada-type cross coupling reactions, cocatalyzed by copper(I) iodide, with electronically activated aryl halides in the presence of an electron withdrawing ortho or meta substituent and an ester group. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) 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. 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.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold was written by Chen, Yin-Bo;Li, Ji-Ling;Shao, Xu-Sheng;Xu, Xiao-Yong;Li, Zhong. And the article was included in Chinese Chemical Letters in 2013.Computed Properties of C8H4BrF3O3 This article mentions the following:

A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized, in which the N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned. Preliminary bioassays indicated that half of the title compounds were endowed with good insecticidal activities against armyworm (Mythimna separata) at 500 mg/L. Exhilaratingly, one of the synthesized compounds was also active against Tetranychus cinnabarinus at 100 mg/L. The difference in activities between the target compounds was influenced by the substituents, which provided some hints for further investigation on structure modifications. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-(trifluoromethoxy)benzoic acid (cas: 453565-90-7Computed Properties of C8H4BrF3O3).

3-Bromo-5-(trifluoromethoxy)benzoic acid (cas: 453565-90-7) 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. 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.Computed Properties of C8H4BrF3O3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of novel fluorophenyl, furan tagged benzylthiopyrimidine derivatives was written by Maddila, Suresh;Lavanya, Palakondu;Jonnalagadda, Sreekanth B.. And the article was included in Chemija in 2013.Application of 76437-44-0 This article mentions the following:

A series of 6-(4-fluorophenyl)-2-(substituted benzylthio)-4-(furan-2-yl)-1,6- dihydropyrimidine derivatives I (R = H, 3-F, 4-CH₃, 4-NO₂, etc.) have been synthesized from 2-acetylfuran through a multi-step reaction sequence. The key intermediate II reacted with various substituted benzyl bromides in the presence of K₂CO₃ to afford the desired products, which were characterized by IR, ¹H NMR, LCMS, and elemental anal. In the experiment, the researchers used many compounds, for example, 1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0Application of 76437-44-0).

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). 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.Application of 76437-44-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design and Synthesis of Benzenesulfonamide Derivatives as Potent Anti-Influenza Hemagglutinin Inhibitors was written by Tang, Guozhi;Lin, Xianfeng;Qiu, Zongxing;Li, Wentao;Zhu, Lei;Wang, Lisha;Li, Shaohua;Li, Haodong;Lin, Wenbin;Yang, Mei;Guo, Tao;Chen, Li;Lee, Daniel;Wu, Jim Z.;Yang, Wengang. And the article was included in ACS Medicinal Chemistry Letters in 2011.Name: 3-Bromo-5-chlorophenylamine This article mentions the following:

Structural optimization of salicylamide-based hemagglutinin (HA) inhibitor 1 resulted in the identification of cis-3-(5-hydroxy-1,3,3-trimethylcyclohexylmethylamino)benzenesulfonamide 28 and its derivatives as potent anti-influenza agents. The lead compound 28 and its 2-chloro analog 40 can effectively prevent cytopathic effects (CPE) caused by infection of influenza A/Weiss/43 strain (H1N1) with EC₅₀ values of 210 and 86 nM, resp. Mechanism of action studies indicate that 40 and its analogs inhibit the virus fusion with host endosome membrane by binding to HA and stabilizing the prefusion HA structure. With significantly improved metabolic stability, the reported series represents the first generation of orally bioavailable HA inhibitors that have a good selectivity window and potential for further development as novel anti-influenza agents. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-chlorophenylamine (cas: 96558-78-0Name: 3-Bromo-5-chlorophenylamine).

3-Bromo-5-chlorophenylamine (cas: 96558-78-0) 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鑱砨romine bond is electrophilic in nature. 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.Name: 3-Bromo-5-chlorophenylamine

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fluorination of orthothioesters through oxidative desulfurization-fluorination was written by Furuta, Satoru;Kuroboshi, Manabu;Hiyama, Tamejiro. And the article was included in Bulletin of the Chemical Society of Japan in 1998.Reference of 57293-19-3 This article mentions the following:

The oxidative desulfurization-fluorination of orthothioesters of type RCH₂C(SMe)₃ using n-Bu₄NH₂F₃ and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF₂SMe in good yields. The products were converted into bromodifluoro olefins RCBr:CF₂ via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)₃ or RCH(OAc)C(SMe)₃ were fluorinated to afford difluoro ketones RCOCF₂SMe or difluoro acetates RCH(OAc)CF₂SMe, resp. The difluoro acetates were reduced to RCH(OAc)CF₂H by radical reduction The mechanisms are discussed for difluorination accompanied by bromination or oxidation 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. 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.Reference of 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of Orally Available Runt-Related Transcription Factor 3 (RUNX3) Modulators for Anticancer Chemotherapy by Epigenetic Activation and Protein Stabilization was written by Yang, Jee Sun;Lee, Chulho;Cho, Misun;Kim, Hyuntae;Kim, Jae Hyun;Choi, Seonghwi;Oh, Soo Jin;Kang, Jong Soon;Jeong, Jin-Hyun;Kim, Hyun-Jung;Han, Gyoonhee. And the article was included in Journal of Medicinal Chemistry in 2015.Category: bromides-buliding-blocks This article mentions the following:

Recently, the authors identified a novel strategy for anticancer chemotherapy by restoring runt-related transcription factor 3 (RUNX3) levels via lactam-based histone deacetylase (HDAC) inhibitors that stabilize RUNX3. Described here are the synthesis, biol. evaluation, and pharmacokinetic evaluation of new synthetic small mols. based on pyridone-based HDAC inhibitors that specifically stabilize RUNX3 by acetylation and regulate its function. Many of the newly synthesized compounds showed favorable RUNX activities, HDAC inhibitory activities, and inhibitory activities on the growth of human cancer cell lines. Notably, one of these new derivatives, I , significantly restored RUNX3 in a dose-dependent manner and showed high metabolic stability, a good pharmacokinetic profile with high oral bioavailability and long half-life, and strong antitumor activity. This study suggests that pyridone-based analogs modulate RUNX3 activity through epigenetic regulation as well as strong transcriptional and post-translational regulation of RUNX3 and could be potential clin. candidates as orally available RUNX3 modulators for the treatment of cancer. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Category: bromides-buliding-blocks).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary