Month: February 2023

Fluorine-Substituted Pyrrolo[2,3-d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis was written by Ravindra, Manasa;Wilson, Mike R.;Tong, Nian;OConnor, Carrie;Karim, Mohammad;Polin, Lisa;Wallace-Povirk, Adrianne;White, Kathryn;Kushner, Juiwanna;Hou, Zhanjun;Matherly, Larry H.;Gangjee, Aleem. And the article was included in Journal of Medicinal Chemistry in 2018.Synthetic Route of C8H6BrFO2 This article mentions the following:

Novel fluorinated 2-amino-4-oxo-6-substituted pyrrolo[2,3-d]pyrimidine analogs were synthesized and tested for selective cellular uptake by folate receptors (FRs) α and β or the proton-coupled folate transporter (PCFT) and for antitumor efficacy. Compounds I (n = 0, 1) and II (n = 0, 1) showed increased in vitro anti-proliferative activities (âˆ?1-fold) over the nonfluorinated analogs toward engineered Chinese hamster ovary and HeLa cells expressing FRs or PCFT. Compounds I (n = 0, 1) and II (n = 0, 1) also inhibited proliferation of IGROV1 and A2780 epithelial ovarian cancer cells; in IGROV1 cells with knockdown of FRα, I (n = 0) and II (n = 0, 1) showed sustained inhibition associated with uptake by PCFT. All compounds inhibited glycinamide ribonucleotide formyltransferase, a key enzyme in the de novo purine biosynthesis pathway. Mol. modeling studies validated in vitro cell-based results. NMR evidence supports the presence of an intramol. fluorine-hydrogen bond. Potent in vivo efficacy of II (n = 1) was established with IGROV1 xenografts in severe compromised immunodeficient mice. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Synthetic Route of C8H6BrFO2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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.Synthetic Route of C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Halogenation using quaternary ammonium polyhalides. VI. Bromination of aromatic amines by use of benzyltrimethylammonium tribromide was written by Kajigaeshi, Shoji;Kakinami, Takaaki;Inoue, Kazuhisa;Kondo, Manabu;Nakamura, Hiroko;Fujikawa, Masahiro;Okamoto, Tsuyoshi. And the article was included in Bulletin of the Chemical Society of Japan in 1988.Category: bromides-buliding-blocks This article mentions the following:

The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane-methanol containing calcium carbonate powder for 0.5 h at room temperaturegave bromo-substituted aromatic amines in good yields. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7Category: bromides-buliding-blocks).

2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7) 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes was written by Li, Songyi;Lian, Chang;Yue, Guanglu;Zhang, Jianning;Qiu, Di;Mo, Fanyang. And the article was included in Journal of Organic Chemistry in 2022.Related Products of 4457-67-4 This article mentions the following:

A transition metal free stannylation reaction of alkyl bromides and iodides with hexamethyldistannane was developed. This protocol is operationally convenient and features a rapid reaction and good functional group tolerance. A wide range of functionalized primary and secondary alkyl and benzyl tri-Me stannanes were prepared in moderate to excellent yields. The success of the gram-scale procedure and tandem Stille coupling reaction has allowed this protocol to demonstrate potential for application in organic synthesis. Both exptl. and theor. studies reveal the mechanistic details of this stannylation reaction. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Related Products of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. 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.Related Products of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Production of halogenated compounds by Bjerkandera adusta was written by Spinnler, H.-E.;de Jong, E.;Mauvais, G.;Semon, E.;le Quere, J.-L.. And the article was included in Applied Microbiology and Biotechnology in 1994.Synthetic Route of C8H6Br2O2 This article mentions the following:

The white-rot fungus Bjerkandera adusta produces volatile chlorinated Ph compounds The main compounds identified were 3-chloro-4-methoxybenzaldehyde (3-chloro-p-anisaldehyde), 3-chloro-4-methoxybenzyl alc. (3-chloro-p-anisyl alc.), 3,5-dichloro-4-methoxybenzaldehyde (3,5-dichloro-p-anisaldehyde), and 3,5-dichloro-4-methoxybenzyl alc. (3,5-dichloro-p-anisyl alc.). P-Anisaldehyde, veratraldehyde, and the corresponding alcs., p-anisyl alc. and veratryl alc., were produced simultaneously. Even with a very low concentration of Cl^– in the medium (<10^-5 M), chlorinated aromatic compounds were still observed Addition of Br^– to the culture medium led to the production of brominated compounds: 3-bromo-4-methoxybenzaldehyde, 3-bromo-4-methoxybenzyl alc., 3,5-dibromo-4-methoxybenzaldehyde, and 3-bromo-5-chloro-4-methoxybenzaldehyde. These brominated compounds have not previously been reported as natural products. Although iodo-aromatic compounds were not produced by supplementation of the medium with I^–, isovanillin was found in the culture broth under these conditions. This compound may be formed by substitution of the I intermediate by an OH group on C3 of the ring. CH₂I₂ or CH₂ClI were also found. This is the 1st time that the production of halomethane has been related to the production of halogenated aromatic compounds All the strains tested have these capabilities. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Synthetic Route of C8H6Br2O2).

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.Synthetic Route of C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Amphiphilic dendrimers with heteroleptic bis([2,2′:6′,2”]terpyridine)-ruthenium(II) cores was written by Joester, Derk;Gramlich, Volker;Diederich, Francois. And the article was included in Helvetica Chimica Acta in 2004.Category: bromides-buliding-blocks This article mentions the following:

Dendrimers were assembled through formation of homo- and heteroleptic Ru^II complexes with [2,2′:6′,2”]terpyridine ligands bearing hydrophilic and hydrophobic dendrons (I; R = C₁₂H₂₅ (11), C(CH₂CH₂CO₂Bu^t)₃ (13), C(CH₂CH₂CONHC₁₂H₂₅)₃ (14)), with the aim to develop amphiphilic vectors for potential use in gene delivery (Scheme 1). The synthesis started with the preparation of the 4′-(3,5-dihalo-4-methoxyphenyl)-[2,2′:6′,2”]terpyridine ligands via the Kroehnke pyridine synthesis, followed by attachment of dendrons by Sonogashira cross-coupling to give the dendritic ligands I (R = C₁₂H₂₅, C(CH₂CH₂CO₂Bu^t)₃, C(CH₂CH₂CONHC₁₂H₂₅)₃, C(CH₂CH₂CO₂^tBu)₃, C(CH₂CH₂CONHC(CH₂XH₂NHBoc)₃)₃, c(CH₂CH₂CONHC(CH₂CH₂CONHC₁₂H₂₅)₃)₃). Ligands were subsequently introduced into the coordination sphere of Ru^III to give the stable intermediates [Ru(11)Cl₃] (24) and [Ru(14)Cl₃] (27). These were transformed under reductive conditions into the heteroleptic complexes [Ru(11)(13)](PF₆)₂ (25) and [Ru(13)(14)](PF₆)₂ (29). Removal of the (tert-butoxy)carbonyl (Boc) protecting groups in 25 and 29 then gave the desired amphiphilic dendrimers with branchings of generations 0 and 1. Complex formation was analyzed by high-resolution matrix-assisted laser-desorption-ionization Fourier-transform ion-cyclotron-resonance mass spectrometry (HR-MALDI-FT-ICR-MS), which provided spectra featuring unique fragment-ion series and perfectly resolved isotope distribution patterns. The preparation of homo- and heteroleptic complexes with terpyridine ligands bearing generation-2 dendrons failed due to steric hindrance by the bulky wedges. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Category: bromides-buliding-blocks).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Phenazine syntheses. VII. Certain disubstituted phenazines was written by Vivian, Donald L.. And the article was included in Journal of Organic Chemistry in 1956.Name: 1-Bromo-4-methoxybutane This article mentions the following:

Disubstituted phenazines are prepared by ring closure of substituted 2-nitrodiphenylamines. Refluxing 25 g. 2,6-(O₂N)₂C₆H₃Cl, 24 g. p-MeOC₆H₄NH₂, 37.5 g. NaOAc.3H₂O, and 375 cc. 95% EtOH 16 hrs. yields 91% 2,6-dinitro-4′-methoxydiphenylamine, small yellowish red needles, m. 171-3°, which (1 g.), heated 20 min. at 250-62° with (CO₂)₂Fe.2H₂O (I) and 10 g. granulated Pb (II), gives 0.15 g. 7-methoxy-1-nitrophenazine, yellowish needles, m. 235-6°. Heating 76.5 g. N,N-dimethyl-p-phenylenediamine, 96 g. 2,5-(O₂N)₂C₆H₃Cl, and 90 g. anhydrous NaOAc 40 hrs. at 195-210°, steam distg, the mixture, adding 100 cc. HCl, steam distilling it again, and extracting the distillation residue with Et₂O give 60 g. 4-chloro-4′-dimethylamino-2-nitrodiphenylmine, brick-red microcrystals, m. 144-6°, which (1 g.), heated with 1.3 g. I and 10 g. II 10-15 min. at 250-60°, yields 0.4 g. 2-chloro-8-dimethylaminophenazine, brownish red needles, m. 194-5°. Refluxing 20 g. 4,5-dinitroveratrole, 24.5 g. PhNH₂, and 40 cc. absolute EtOH 3 weeks, steam distilling the mixture, and chromatographing the product on Al₂O₃ give 17.4 g. 4,5-dimethoxy-2-nitrodiphenylamine, orange needles, m. 120.5-1.5°, which (2 g.) heated 15 min. at 255-60° with 2.6 g. I and 20 g. II, yields 0.43 g. 2,3-dimethoxyphenazine, light yellow needles, m. 280-1°. Heating 28.1 g. 2,5-Br₂C₆H₃NO₂, 20.2 g. 5-bromo-2-anisidine, and 30 g. anhydrous NaOAc 40 hrs. at 200-10° yields 30.2 g. 4,5′-dibromo-2′-methoxy-2-nitrodiphenylamine, small red-orange needles, m. 198-200°, which (2 g.), heated 12 min. at 260° with 2.6 g. I and 20 g. II, yields 0.8 g. 2,7-dibromophenazine, bright yellow needles or prisms, m. 251-2°. Heating 200 g. 2,5-Cl₂C₆H₃NO₂, 200 g. o-MeC₆H₄NH₂, and 200 g. NaOAc 40 hrs. at 180° gives 20.5% 4-chloro-2′-methyl-2-nitrodiphenylamine, orange prisms, m. 103-5°, which (10 g.), heated with 12 g. I and 100 g. II 12 min. at 270°, yields 3.5 g. 7-chloro-1-methylphenazine, yellow needles, m. 28-9°. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Name: 1-Bromo-4-methoxybutane).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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.Name: 1-Bromo-4-methoxybutane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

1,2-Bis(diphenylphosphino)ethane (dppe)/NBS: An Unprecedented Combination for Deoxygenation of Sulfoxides Under Mild Conditions was written by Joshi, Asha;Iqbal, Zafar;De, Saroj Ranjan. And the article was included in ChemistrySelect in 2022.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

A novel, efficient and metal-free strategy for the deoxygenation of sulfoxides to sulfides was disclosed under mild conditions using dppe/NBS reagent system. Among several developed methods using phosphine based ligands, very few are convenient as most of them are confined to harsh reaction conditions, inseparable side products, moderate yields, and the use of costly and toxic reagents. The developed dppe/NBS promoted deoxygenation strategy tolerates a wide range of functional groups to afford good yields of desired sulfides. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application In Synthesis of 1-Bromopyrrolidine-2,5-dione).

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. 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 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies was written by Kongkathip, Boonsong;Hasakunpaisarn, Anuch;Boonananwong, Suthinee;Kongkathip, Ngampong. And the article was included in Steroids in 2010.Product Details of 28322-40-9 This article mentions the following:

In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogs with different side chains and degrees of oxidation at C-9, e.g. I, were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biol. activity, the existence of a ketone functional at C-9 is also crucial for anticancer activity whereas hydroxyl/ketone function at C-22 on the side chain did not increase cytotoxicity. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Product Details of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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.Product Details of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rational Development of 4-Aminopyridyl-Based Inhibitors Targeting Trypanosoma cruzi CYP51 as Anti-Chagas Agents was written by Choi, Jun Yong;Calvet, Claudia M.;Gunatilleke, Shamila S.;Ruiz, Claudia;Cameron, Michael D.;McKerrow, James H.;Podust, Larissa M.;Roush, William R.. And the article was included in Journal of Medicinal Chemistry in 2013.Name: Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

A new series of 4-aminopyridyl-based lead inhibitors targeting Trypanosoma cruzi CYP51 (TcCYP51) has been developed using structure-based drug design as well as structure-property relationship (SPR) analyses. The screening hit starting point, LP10 (K_D â‰?42 nM; EC₅₀ = 0.65 μM), has been optimized to give the potential leads 14t, 27i, 27q, 27r, and 27t, which have low-nanomolar binding affinity to TcCYP51 and significant activity against T. cruzi amastigotes cultured in human myoblasts (EC₅₀ = 14-18 nM for 27i and 27r). Many of the optimized compounds have improved microsome stability, and most are selective against human CYPs 1A2, 2D6, and 3A4 (<50% inhibition at 1 μM). A rationale for the improvement in microsome stability and selectivity of inhibitors against human metabolic CYP enzymes is presented. In addition, the binding mode of 14t with the Trypanosoma brucei CYP51 (TbCYP51) orthologue has been characterized by X-ray structure anal. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Name: Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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). 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.Name: Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of S-Nitrosoglutathione Reductase Inhibitors: Potential Agents for the Treatment of Asthma and Other Inflammatory Diseases was written by Sun, Xicheng;Wasley, Jan W. F.;Qiu, Jian;Blonder, Joan P.;Stout, Adam M.;Green, Louis S.;Strong, Sarah A.;Colagiovanni, Dorothy B.;Richards, Jane P.;Mutka, Sarah C.;Chun, Lawrence;Rosenthal, Gary J.. And the article was included in ACS Medicinal Chemistry Letters in 2011.Application of 35065-86-2 This article mentions the following:

S-Nitrosoglutathione reductase (GSNOR) regulates S-nitrosothiols (SNOs) and nitric oxide (NO) in vivo through catabolism of S-nitrosoglutathione (GSNO). GSNOR and the anti-inflammatory and smooth muscle relaxant activities of SNOs, GSNO, and NO play significant roles in pulmonary, cardiovascular, and gastrointestinal function. In GSNOR knockout mice, basal airway tone is reduced and the response to challenge with bronchoconstrictors or airway allergens is attenuated. Consequently, GSNOR has emerged as an attractive therapeutic target for several clin. important human diseases. As such, small mol. inhibitors of GSNOR were developed. These GSNOR inhibitors were potent, selective, and efficacious in animal models of inflammatory disease characterized by reduced levels of GSNO and bioavailable NO. N6022, a potent and reversible GSNOR inhibitor, reduced bronchoconstriction and pulmonary inflammation in a mouse model of asthma and demonstrated an acceptable safety profile. N6022 is currently in clin. development as a potential agent for the treatment of acute asthma. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Application of 35065-86-2).

3-Bromophenyl acetate (cas: 35065-86-2) 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 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.Application of 35065-86-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary