Tag: 200-300

Efficient and Regioselective Synthesis of Phenothiazine via Ferric Citrate Catalyzed C-S/C-N Cross-Coupling was written by Das, Tonmoy Chitta;Imam Quadri, Syed Aziz;Farooqui, Mazahar. And the article was included in Letters in Organic Chemistry in 2019.SDS of cas: 82702-31-6 This article mentions the following:

Efficient C-S and C-N cross-coupling reactions have been developed for regioselective, scalable and environmentally benign synthesis of substituted phenothiazine derivatives I (R = H, CN, COOMe, CONH₂, Cl, COOH, Br, CF₃). Cross-coupling reactions were demonstrated on various challenging substrates using non-toxic, highly economical, readily available ferric citrate as a catalyst to get desired products I with high regioselectivity. Atom economy is the added advantage of this protocol since addnl. N-protection step before coupling and eventual deprotection of the same to obtain the desired product are not required. This is the first report on the use of inexpensive ferric citrate as a catalyst without involving any ligand for the synthesis of regioselectively substituted phenothiazines I. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6SDS of cas: 82702-31-6).

Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6) 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.SDS of cas: 82702-31-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, Synthesis, and Evaluation of Novel Auxin Mimic Herbicides was written by Do-Thanh, Chi-Linh;Vargas, Jose J.;Thomas, Joseph W.;Armel, Gregory R.;Best, Michael D.. And the article was included in Journal of Agricultural and Food Chemistry in 2016.Application In Synthesis of Methyl 3-bromo-5-hydroxybenzoate This article mentions the following:

Due to the key roles of auxins as master regulators of plant growth, there is considerable interest in the development of compounds with auxin-like properties for growth management and weed control applications. Herein, we describe the design and multistep synthesis of ten compounds bearing combinations of functional groups commonly associated with auxin-type properties. Following synthesis, these compounds were tested against multiple weed species as well as sweet corn. In general, while these structures were not quite as active as com. auxin mimic herbicides, multiple compounds exhibited broadleaf weed activity with concurrent selectivity in sweet corn (Zea mays L. var. saccharum). In addition, differential results were observed upon subtle changes to structure, providing insights into the structural properties required for activity. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1Application In Synthesis of Methyl 3-bromo-5-hydroxybenzoate).

Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1) 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.Application In Synthesis of Methyl 3-bromo-5-hydroxybenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Copper-Mediated Deuterotrifluoromethylation of 浼?Diazo Esters was written by Hu, Mingyou;Xie, Qiqiang;Li, Xinjin;Ni, Chuanfa;Hu, Jinbo. And the article was included in Chinese Journal of Chemistry in 2016.Electric Literature of C10H11BrO2 This article mentions the following:

A copper-mediated deuterotrifluoromethylation of 浼?diazo esters RC(=N₂)CO₂CH₂CH₃ (R = C₆H₅, 4-BrC₆H₄CH₂, octanyl, naphth-1-yl, etc.) under the promotion of deuterium oxide (D₂O) has been developed for the synthesis of deuterium-labeled trifluoromethyl compounds RC(CF₃)(D)(CO₂CH₂CH₃). This deuterotrifluoromethylation reaction is of broad scope and can afford the deuterated products with higher than 99% isotopic purity. Moreover, the results of this investigation also provide some exptl. evidences to support the previously proposed trifluoromethylation mechanism. In the experiment, the researchers used many compounds, for example, Ethyl (2-bromophenyl)acetate (cas: 2178-24-7Electric Literature of C10H11BrO2).

Ethyl (2-bromophenyl)acetate (cas: 2178-24-7) 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.Electric Literature of C10H11BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of (3S,3aR)-2-(3-Chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic Acid (PF-3882845), an Orally Efficacious Mineralocorticoid Receptor (MR) Antagonist for Hypertension and Nephropathy was written by Meyers, Marvin J.;Arhancet, Graciela B.;Hockerman, Susan L.;Chen, Xiangyang;Long, Scott A.;Mahoney, Matthew W.;Rico, Joseph R.;Garland, Danny J.;Blinn, James. R.;Collins, Joe T.;Yang, Shengtian;Huang, Horng-Chih;McGee, Kevin F.;Wendling, Jay M.;Dietz, Jessica D.;Payne, Maria A.;Homer, Bruce L.;Heron, Marcia I.;Reitz, David B.;Hu, Xiao. And the article was included in Journal of Medicinal Chemistry in 2010.Synthetic Route of C9H6BrF3O3 This article mentions the following:

We have discovered a novel class of nonsteroidal pyrazoline antagonists of the mineralocorticoid receptor (MR) that show excellent potency and selectivity against other nuclear receptors. Early analogs were poorly soluble and had a propensity to inhibit the hERG channel. Remarkably, both of these challenges were overcome by incorporation of a single carboxylate moiety. Structural modification of carboxylate-containing lead R-4g with a wide range of substituents at each position of the pyrazoline ring resulted in R-12o, which shows excellent activity against MR and reasonable pharmacokinetic profile. Introduction of conformational restriction led to a novel series characterized by exquisite potency and favorable steroid receptor selectivity and pharmacokinetic profile. Oral dosing of 3S,3aR-27d (PF-3882845) in the Dahl salt sensitive preclin. model of salt-induced hypertension and nephropathy showed blood pressure attenuation significantly greater than that with eplerenone, reduction in urinary albumin, and renal protection. As a result of these findings, 3S,3aR-27d was advanced to clin. studies. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-(trifluoromethoxy)benzoate (cas: 933785-18-3Synthetic Route of C9H6BrF3O3).

Methyl 4-bromo-2-(trifluoromethoxy)benzoate (cas: 933785-18-3) 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. Synthetic Route of C9H6BrF3O3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Photoinduced electron transfer quenching and sugar effects on the electrostatic interaction between an anionic Ru(II) complex and cationic bipyridinium derivatives functionalized with boronic acids was written by Uddin, Jamal Md.;DiCesare, Nicolas;Lakowicz, Joseph R.. And the article was included in Inorganica Chimica Acta in 2012.Formula: C12H16BBrO2 This article mentions the following:

The photoinduced electron transfer quenching of an anionic ruthenium(II) metal-ligand-complex (Ru(dpp(SO₃Na)))₂(mcbpy)Cl₂ by two boronic acid functionalized benzyl viologen (BV²⁺) derivatives has been investigated as well as their response to sugar. The electrostatic interaction between these two charge species lead to the formation of static quenching which is removed in presence of sugar due to the formation of a neutral zwitterionic quencher. Spectral data, quenching parameters and sugar titration curves are presented and discussed in term of future developments of optical sensors for sugar. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Formula: C12H16BBrO2).

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. 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.Formula: C12H16BBrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides was written by Yang, Chu-Ting;Zhang, Zhen-Qi;Tajuddin, Hazmi;Wu, Chen-Cheng;Liang, Jun;Liu, Jing-Hui;Fu, Yao;Czyzewska, Maria;Steel, Patrick G.;Marder, Todd B.;Liu, Lei. And the article was included in Angewandte Chemie, International Edition in 2012.COA of Formula: C13H14BrNO2 This article mentions the following:

Authors have developed an unprecedented copper-catalyzed cross-coupling reaction of unactivated alkyl halides and pseudohalides with diboron reagents. This reaction can be used to prepare primary and secondary alkylboronic esters with diverse structures and functional groups, many of which would be difficult to access by other means. The reaction is efficient, practically simple, and gives easy isolation of the products which can be further enhanced through the use of polymer-supported ligands. It is also reported a mild and practical protocol for the Suzuki-Miyaura coupling of alkylboronic esters with both aryl bromides and chlorides. 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. 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. 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

Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation was written by Zhong, Dayou;Wu, Di;Zhang, Yan;Lu, Zhiwu;Usman, Muhammad;Liu, Wei;Lu, Xiuqiang;Liu, Wen-Bo. And the article was included in Organic Letters in 2019.Safety of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chem. A direct synthesis of sultams by an intramol. C(sp³)-H amidation reaction using an iron complex in situ derived from Fe(ClO₄)₂ and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Safety of 1-(3-Bromopropyl)-4-methoxybenzene).

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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. 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.Safety of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and Structure-Activity Relationships of Stilbene Retinoid Analogs Substituted with Heteroaromatic Carboxylic Acids was written by Beard, Richard L.;Colon, Diana F.;Gillett, Samuel J.;Henry, Elizabeth;Marler, Deborah K.;Song, Tae;Denys, Lydia;Garst, Michael E.;Arefieg, Taghreed. And the article was included in Journal of Medicinal Chemistry in 1995.Computed Properties of C8H7BrO2 This article mentions the following:

Retinoids elicit biol. responses by activating a series of nuclear receptors. Six retinoid receptors belonging to two families are currently known: retinoic acid receptors (RAR_{浼?灏?and绾?/sub>) and retinoid X receptors (RXR浼?灏?and绾?/sub>). Stilbene retinoid analogs of retinoic acid (RA), such as (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propen-1-yl]benzoic acid (TTNPB) and (E)-4-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)propen-1-yl]benzoic acid (3-methyl-TTNPB) (I), display differential RAR and RXR activities, depending on the substituent at C3 of the naphthalene ring. The authors report here structural modifications of the benzoate moiety of I that result in analogs with greater RXR selectivity as well as those with pan-agonist (activate both RAR and RXR receptors) activities, analyze the structural features that impart receptor selectivity, and describe a stereoselective method for the synthesis of these analogs. The biol. activities associated with the RAR and RXR receptors were examined by testing representative examples with different receptor activation profiles for their ability to induce tissue transglutaminase (Tgase) activity in a human promyelocytic leukemia cell line (HL-60 cdm-1) and to inhibit tumor-promoter-induced ornithine decarboxylase (ODC) activity in hairless mouse skin. These results suggest that RAR agonists and RXR agonists may have different therapeutic applications. Finally, the authors show that RXR agonists are significantly reduced in teratogenic potency relative to RAR agonists and may therefore have significant advantages in clin. practice. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Computed Properties of C8H7BrO2).}

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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 C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-Activity Relationship Probing of the Natural Marine Antifoulant Barettin was written by Labriere, Christophe;Cervin, Gunnar;Pavia, Henrik;Hansen, Joern H.;Svenson, Johan. And the article was included in Marine Biotechnology in 2021.Category: bromides-buliding-blocks This article mentions the following:

In the current study the antifouling activity of 29 synthetic analogs e.g., I designed and inspired by the potent antifouling effect seen for benzo[g]dipodazine were reported. The library contains mainly not only dipodazine derivatives but also disubstituted diketopiperazines and compounds incorporating alternative heterocyclic cores such as hydantoin, creatinine, and rhodanine. Several of the prepared compounds inhibit the settlement of Amphibalanus improvisus cyprids at low micromolar concentrations, in parity with the natural barettin. While several highly active compounds were prepared by incorporating the benzo[g]indole as hydrophobic substituent, the remarkable antifouling effect reported for benzo[g]dipodazine was not observed when evaluated in the study. 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Crystal-Packing Trends for a Series of 6,9,12,15,18-Pentaaryl-1-hydro[60]fullerenes was written by Kennedy, Robert D.;Halim, Merissa;Khan, Saeed I.;Schwartz, Benjamin J.;Tolbert, Sarah H.;Rubin, Yves. And the article was included in Chemistry – A European Journal in 2012.Name: 4-Bromo-4′-tert-butylbiphenyl This article mentions the following:

The relationship between the size of the substituents of aryl groups in a series of fifteen 6,9,12,15,18-pentaaryl-1-hydro[60]fullerenes and the solid-state structures and packing motifs of these compounds has been analyzed. Pentaarylfullerenes have a characteristic “badminton shuttlecock” shape that causes several derivatives to crystallize into columnar stacks. However, many pentaarylfullerenes form non-stacked structures with, for example, dimeric, layered, diamondoid, or feather-in-cavity relationships between mols. Computational modeling gave a qual. estimate of the best shape match between the ball and socket surfaces of each pentaarylfullerene. The best match was for pentaarylfullerenes with large, spherically shaped para-substituents on the aryl groups. The series of pentaarylfullerenes was characterized by single-crystal X-ray diffraction. A total of 34 crystal structures were obtained as various solvates and were categorized by their packing motifs. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1Name: 4-Bromo-4′-tert-butylbiphenyl).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) 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. Name: 4-Bromo-4′-tert-butylbiphenyl

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary