Tag: 200-300

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

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

Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells was written by Hampel, Sonja M.;Sidibe, Assitan;Gunaratnam, Mekala;Riou, Jean-Francois;Neidle, Stephen. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.COA of Formula: C13H14BrNO2 This article mentions the following:

A series of tetrasubstituted naphthalene diimide compounds I (n = 2-4) with N-methylpiperazine end groups has been synthesized and evaluated as G-quadruplex ligands. They have high affinity and selectivity for telomeric G-quadruplex DNA over duplex DNA. CD studies show that they induce formation of a parallel G-quadruplex topol. They inhibit the binding of hPOT1 and topoisomerase IIIα to telomeric DNA and inhibit telomerase activity in MCF7 cells. I has potent activity in a panel of cancer cell lines, with typical IC₅₀ values of âˆ?.1 μM, and up to 100-fold lower toxicity in a normal human fibroblast cell line. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4COA of Formula: C13H14BrNO2).

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. 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.COA of Formula: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Gold(I)-Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone-Fused Polycyclic Molecules was written by Yu, Congjun;Chen, Bin;Zhou, Tian;Tian, Qingshan;Zhang, Guozhu. And the article was included in Angewandte Chemie, International Edition in 2015.Electric Literature of C8H4BrF3O This article mentions the following:

An efficient and convenient synthesis of useful linear cyclopentenone-fused polycyclic compounds has been achieved through a novel gold(I)-catalyzed transformation of diynes. The method demonstrates high product yields and tolerates of a wide variety of important functional groups. Gold-vinylidene formation, methoxy group migration, and Nazarov-type cyclization are proposed to be the key steps in the reaction pathway. The synthetic utility of this method is demonstrated by converting the product to eight-membered-ring-fused compound In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Electric Literature of C8H4BrF3O).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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.Electric Literature of C8H4BrF3O

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of a novel [3.2.1] benzo fused bicyclic sulfonamide-pyrazoles as potent, selective and efficacious γ-secretase inhibitors was written by Ye, Xiaocong M.;Konradi, Andrei W.;Sun, Minghua;Yuan, Shendong;Aubele, Danielle L.;Dappen, Michael;Dressen, Darren;Garofalo, Albert W.;Jagodzinski, Jacek J.;Latimer, Lee;Probst, Gary D.;Sham, Hing L.;Wone, David;Xu, Ying-zi;Ness, Daniel;Brigham, Elizabeth;Kwong, Grace T.;Willtis, Chris;Tonn, George;Goldbach, Erich;Quinn, Kevin P.;Zhang, Hongbin H.;Sauer, John-Michael;Bova, Michael;Basi, Guriqbal S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Computed Properties of C8H4BrF3O This article mentions the following:

Structure-activity relation (SAR) of a novel, potent and metabolically stable series of benzo [3.2.1] bicyclic sulfonamide-pyrazoles as γ-secretase inhibitors are described. Compounds that are efficacious in reducing the cortical Aβx-40 levels in FVB mice via oral dose, as well as those with high selectivity over Notch, are highlighted. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Computed Properties of C8H4BrF3O).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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). 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 C8H4BrF3O

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-catalyzed alkoxycarbonylation of unactivated secondary alkyl bromides at low pressure was written by Sargent, Brendon T.;Alexanian, Erik J.. And the article was included in Journal of the American Chemical Society in 2016.Formula: C10H13BrO This article mentions the following:

Catalytic carbonylations of organohalides are important C-C bond formations in chem. synthesis. Carbonylations of unactivated alkyl halides remain a challenge and currently require the use of alkyl iodides under harsh conditions and high pressures of CO. Herein we report a palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides that proceeds at low pressure (2 atm CO) under mild conditions. Preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. These reactions efficiently deliver esters from unactivated alkyl bromides across a diverse range of substrates and represent the first catalytic carbonylations of alkyl bromides with carbon monoxide. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Formula: C10H13BrO).

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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Formula: C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and anion binding properties of multi-phosphonium triarylboranes: selective sensing of cyanide ions in buffered water at pH 7 was written by Song, Ki Cheol;Lee, Kang Mun;Nghia, Nguyen Van;Sung, Woo Young;Do, Youngkyu;Lee, Min Hyung. And the article was included in Organometallics in 2013.Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene This article mentions the following:

A series of mono-, di-, and tris-phosphonium-substituted triarylboranes, [Mes₂BAr^P]I ([2]I), [MesBAr^P₂]I₂ ([3]I₂), and [BAr^P₃]I₃ ([4]I₃) (Ar^P = 4-MePh₂P⁺-2,6-Me₂C₆H₂), were prepared from the corresponding neutral boranes 2a–4a. The crystal structure of [4]I₃ determined by x-ray diffraction study reveals peripheral decoration of aryl groups with phosphonium moieties. The anion affinity of the cationic boranes for fluoride and cyanide ions was investigated by UV-vis absorption titrations in aqueous solution The triarylboranes, [2]I-[4]I₃ bind both fluoride and cyanide ions in a DMSO/H₂O (7:3 volume/volume) mixture with high binding constants (K). Comparison of the K values of triarylboranes for fluoride reveals that fluorophilicity increases with the increasing number of phosphonium moieties: [2]⁺ (K = 2.3 × 10¹ M^-1) < [3]²⁺ (3.6 × 10⁵ M^-1) < [4]³⁺ (1.0 × 10⁷ M^-1). A similar trend is also observed in the cyanide binding, with K values that are greater by 2-4 orders of magnitude than those in the fluoride binding. These results indicate an apparent additive effect of multiple phosphonium substitutions on the Lewis acidity enhancement of triarylboranes. The triphosphonium borane [4]Cl₃, a water-soluble form of [4]I₃, was further utilized in evaluating the anion affinity in water. While [4]³⁺ is shown to hardly bind fluoride in buffered aqueous solutions at pH 7, it binds cyanide with a high binding constant (1.7 × 10⁷ M^-1). In the experiment, the researchers used many compounds, for example, 2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene).

2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2) 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. 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.Recommanded Product: 2,5-Dibromo-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Halogenated Bis(methoxybenzylidene)-4-piperidone Curcuminoids with Improved Anticancer Activity was written by Schmitt, Florian;Subramaniam, Dharmalingam;Anant, Shrikant;Padhye, Subhash;Begemann, Gerrit;Schobert, Rainer;Biersack, Bernhard. And the article was included in ChemMedChem in 2018.Formula: C8H6Br2O2 This article mentions the following:

A series of readily available curcuminoids with a halogenated bis(4-methoxy/4,5-dimethoxybenzylidene)-4-piperidone structure were prepared and analyzed for their cytotoxic impact on eight human cancer cell lines of five different entities. The known 3,4,5-trimethoxybenzylidene curcuminoid 2a and the new bis-(3-bromophenyl) and bis-(3,5-dibromophenyl) derivatives 3c ((E)-1-ethyl-3,5-bis(3-bromo-4,5-dimethoxybenzylidene)-4-piperidone HCl) and 3d ((E)-1-ethyl-3,5-bis(3,5-dibromo-4-methoxybenzylidene)-4-piperidone HCl) proved to be more strongly antiproliferative than the known curcuminoid EF24 against six of these cell lines. Compounds 2a and 3c caused a distinct increase of reactive oxygen species, which eventually elicited apoptosis in 518A2 melanoma cells. Compound 2a arrested 518A2 melanoma cells in G₁ phase of the cell cycle and had no effect on the expression of pro-metastatic matrix metalloproteinases MMP-2 and MMP-9, whereas 3c led to an accumulation of 518A2 cells in the G₂/M phase and to a downregulation of MMP-2 expression. In addition, treatment with 2a and 3c resulted in significant inhibition of colony formation in HCT116 cells. Both 2a and 3c showed antiangiogenic activity, for example, by inhibiting the formation of sub-intestinal veins (SIV) in zebrafish embryos. Compound 3c was also well tolerated by mice and inhibited the growth of HCT116 colon cancer xenografts. 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. 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.Formula: C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-catalyzed diastereoselective cross-coupling of two aryl halides via C-H activation: synthesis of chiral eight-membered nitrogen heterocycles was written by Cheng, Cang;Zuo, Xiang;Tu, Dongdong;Wan, Bin;Zhang, Yanghui. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.SDS of cas: 173026-23-8 This article mentions the following:

A method for the synthesis of enantiopure eight-membered nitrogen heterocycles, e.g., I was developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products represented a novel type of chiral scaffold, which feature easy modification and high configurative stability and had the potential to be applied in asym. synthesis. Palladacycles that were formed via the C-H activation of 2-iodobiphenyls should act as the intermediates. The reaction provided a new strategy for the synthesis of medium-sized ring compounds In the experiment, the researchers used many compounds, for example, 2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8SDS of cas: 173026-23-8).

2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8) 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. 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.SDS of cas: 173026-23-8

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