Tag: 200-300

Synthesis of Substituted 6-Anilinouracils and Their Inhibition of DNA Polymerase IIIC and Gram-Positive Bacterial Growth was written by Zhi, Chengxin;Long, Zheng-Yu;Gambino, Joseph;Xu, Wei-Chu;Brown, Neal C.;Barnes, Marjorie;Butler, Michelle;LaMarr, William;Wright, George E.. And the article was included in Journal of Medicinal Chemistry in 2003.Related Products of 615-55-4 This article mentions the following:

Certain substituted 6-anilinouracils are potent and selective inhibitors of Gram+ bacterial DNA polymerase IIIC (pol IIIC). In addition, analogs with 3-substituents in the uracil ring have potent antibacterial activity against Gram+ organisms in culture. In an attempt to find optimal anilino substituents for pol IIIC binding and optimal 3-substituents for antibacterial activity, several series of 3-substituted-6-aminouracils were prepared and assayed their activity against pol IIIC from Bacillus subtilis and a panel of Gram+ and Gram- bacteria in culture. The 6-(3-ethyl-4-methylanilino) group and closely related substituent patterns maximized pol IIIC inhibition potency. Among a series of 3-(substituted-butyl)-6-(3-ethyl-4-methylanilino)uracils, basic amino substituents increased pol IIIC inhibition, but decreased antibacterial activity. The most potent antibacterials were simple hydroxybutyl and methoxybutyl derivatives, and hydrophobically substituted piperidinylbutyl derivatives In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Related Products of 615-55-4).

3,4-Dibromoaniline (cas: 615-55-4) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Related Products of 615-55-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Binding Mode and Potency of N-Indolyloxopyridinyl-4-aminopropanyl-Based Inhibitors Targeting Trypanosoma cruzi CYP51 was written by Vieira, Debora F.;Choi, Jun Yong;Calvet, Claudia M.;Siqueira-Neto, Jair Lage;Johnston, Jonathan B.;Kellar, Danielle;Gut, Jiri;Cameron, Michael D.;McKerrow, James H.;Roush, William R.;Podust, Larissa M.. And the article was included in Journal of Medicinal Chemistry in 2014.Computed Properties of C8H6BrFO2 This article mentions the following:

Chagas disease is a chronic infection in humans caused by Trypanosoma cruzi and manifested in progressive cardiomyopathy and/or gastrointestinal dysfunction. Limited therapeutic options to prevent and treat Chagas disease put 8 million people infected with T. cruzi worldwide at risk. CYP51, involved in the biosynthesis of the membrane sterol component in eukaryotes, is a promising drug target in T. cruzi. We report the structure-activity relationships (SAR) of an N-arylpiperazine series of N-indolyloxopyridinyl-4-aminopropanyl-based inhibitors designed to probe the impact of substituents in the terminal N-Ph ring on binding mode, selectivity and potency. Depending on the substituents at C-4, two distinct ring binding modes, buried and solvent-exposed, have been observed by X-ray structure anal. (resolution of 1.95-2.48 Å). The 5-chloro-substituted analogs 9 and 10 with no substituent at C-4 demonstrated improved selectivity and potency, suppressing ≥99.8% parasitemia in mice when administered orally at 25 mg/kg, b.i.d., for 4 days. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Computed Properties of C8H6BrFO2).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and antibacterial activity of novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain was written by Song, Qiu-Ling;Guo, Bao-Qin;Zhang, Wen;Lan, Ping;Sun, Ping-Hua;Chen, Wei-Min. And the article was included in Journal of Antibiotics in 2011.Application of 954-81-4 This article mentions the following:

A set of 17 novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain were synthesized and evaluated for their antibacterial activities, which the aryltetrazolyl group was selected to replace the hetero-aryl moiety of the side chain in telithromycin for designing new compounds The synthesis of aryltetrazolyl alkylamines was reported in detail. The antibacterial activities of new ketolides were evaluated against a number of pathogens including macrolide-resistant organisms by using telithromycin as the reference Many of the evaluated compounds exhibited remarkable activities against both erythromycin-susceptible and erythromycin-resistant organisms such as Staphylococcus aureus (except S. aureus AD-08), Pseudomonas aeruginosa and Escherichia coli. Among these, the compound 11e exhibited excellent antibacterial potency against all the strains in comparison with others. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Application 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. 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.Application of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An improved total synthesis of spermatinamine, an inhibitor of isoprenylcysteine carboxy methyltransferase was written by Ullah, Nisar;Haladu, Shamsuddeen A.;Mosa, Basem A.. And the article was included in Tetrahedron Letters in 2011.Name: 3,5-Dibromo-4-methoxybenzaldehyde This article mentions the following:

An improved total synthesis of spermatinamine (I), an inhibitor of the anticancer target isoprenylcysteine carboxy methyltransferase (no biol. testing data presented), was accomplished starting from the com. available 3,4-dibromo-4-hydroxybenzaldehyde via a high yielding reaction sequence in an overall yield of 31%. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Name: 3,5-Dibromo-4-methoxybenzaldehyde).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fries reaction of m-halophenylacetate was written by Chen, F.-C.;Chang, K. T.. And the article was included in Taiwan Yaoxue Zazhi in 1952.Category: bromides-buliding-blocks This article mentions the following:

m-BrC₆H₄OAc (I) (10 g.) heated with 20 g. AlCl₃ (II), 2 hrs. at 80°, followed by steam distillation, gave 3 g. yellow crystals (III), m. 42-3°, and 0.4 g. yellow crystals (IV), m. 85-90°, from the distillate and the residue, resp. I (10 g.) treated with 18 g. II, 1 hr. at 45°, gave 1 g. IV. Assuming that the o-isomer predominates at elevated temperature, III and IV are apparently 4-bromo-2-hydroxy- and 2-bromo-4-hydroxyacetophenones, resp. III with BzH gave a chalcone (V), yellow needles, m. 115-16°; cyclization of V with H₃PO₄ gave a flavanone (VI), m. 77-8°; dehydrogenation of VI with N-bromosuccinimide gave a flavone, m. 162-3°. Heating 7 g. m-IC₆H₄OAc (VII) in 35 ml. PhNO₂ (VIII) with 20 g. II 4 hrs. at 90-5°, followed by steam distillation, gave 0.1 g. crystals (IX), m. 53-4°, and 0.1 g. crystals (X), m. 128-36°, from the distillate and the residue, resp. VII (5 g.) in 25 ml. VIII heated with 17 g. II 3 hrs. at 100-120° gave 0.15 g. IX. IX and X are apparently 2-hydroxy-4-iodo- and 4-hydroxy-2-iodoacetophenones, resp. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Category: bromides-buliding-blocks).

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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and Bioevaluation of Novel [¹⁸F]FDG-Conjugated 2-Nitroimidazole Derivatives for Tumor Hypoxia Imaging was written by Yang, Xianteng;Wang, Fan;Zhu, Hua;Yang, Zhi;Chu, Taiwei. And the article was included in Molecular Pharmaceutics in 2019.Product Details of 954-81-4 This article mentions the following:

Hypoxia imaging can guide tumor treatment and monitor changes in hypoxia during treatment. However, there is still no ideal hypoxia imaging agent for clin. applications. In this study, two novel 2-nitromidazole derivatives were synthesized and directly radiolabeled by [¹⁸F]FDG in high radiochem. yield and excellent radiochem. purity. Cell experiments, biodistribution, and positron emission tomog. (PET) imaging studies were also conducted in mice-bearing S180 or OS732 tumors. [¹⁸F]FDG-2NNC2ON [(2R,3S,4R,E)-2-¹⁸F-fluoro-3,4,5,6-tetrahydroxyhexanal O-3-(2-(2-nitro-1H-imidazole-1-yl)ethylamino)-2-oxopropyl oxime] and [¹⁸F]FDG-2NNC5ON [(2R,3S,4R,E)-2-¹⁸F-fluoro-3,4,5,6-tetrahydroxyhexanal-O-3-(5-(2-nitro-1H-imidazole-1-yl)pentylamino)-2-oxopropyl oxime] can be cleared from the blood quickly and specifically target hypoxic tumor cells. The uptake of the probes by hypoxic cells gradually increases with time. After 4 h, the uptake value of [¹⁸F]FDG-2NNC2ON in hypoxic cells is 3.2 times higher than that in normoxia cells. In contrast, there is no difference in the uptake of [¹⁸F]FDG between hypoxic cells and normoxia cells. Biodistribution resulting from two tumor models indicate that the uptake values of the two radiotracers in the tumor are higher at 1 h than those at 2 and 4 h. At 1 and 2 h, the tumors are clearly observed on the PET images and the imaging features of [¹⁸F]FDG-2NNC5ON and [¹⁸F]FDG-2NNC2ON are distinct from those of [¹⁸F]FDG. Compared with [¹⁸F]FDG-2NNC5ON, [¹⁸F]FDG-2NNC2ON has a higher proportion of renal excretion, lower digestive tract uptake, and better imaging contrast because of its higher hydrophilicity. At 2 h, [¹⁸F]FDG-2NNC2ON shows a good tumor-to-blood (T/B) ratio, tumor-to-muscle ratio based on biodistribution (Bio-T/M ratio), and tumor-to-muscle ratio based on regions of interest on the PET images [region of interest (ROI)-T/M ratio] in the two tumor models (T/B, Bio-T/M, and ROI-T/M ratios are 3.2, 2.6, and 3.9 in the S180 tumor model and are 3.4, 4.2, and 4.6 in the OS732 tumor model, resp.). The imaging features visualized with autoradiog. mostly coincided with the pos. areas of HIF1α staining by immunofluorescence. Meanwhile, the biodistribution study and PET imaging revealed that the uptake of the radiotracers in the tumor cannot be competed by 5% glucose, confirming that [¹⁸F]FDG-2NNC2ON targets the hypoxic regions of the tumors instead of targeting tumors through the glucose metabolism pathway. These results suggest that the new 2-nitroimidazole derivative conjugated with [¹⁸F]FDG, [¹⁸F]FDG-2NNC2ON, has potential as an imaging agent for hypoxia. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Product Details 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. 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.Product Details of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

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–bromine 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 α-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 α-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