Month: January 2023

Structure-Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates was written by Avery, Mitchell A.;Alvim-Gaston, Maria;Vroman, Jeffrey A.;Wu, Baogen;Ager, Arba;Peters, Wallace;Robinson, Brian L.;Charman, William. And the article was included in Journal of Medicinal Chemistry in 2002.COA of Formula: C10H13BrO This article mentions the following:

On the basis of earlier reported quant. structure-activity relationship studies, a series of 9β-16-(arylalkyl)-10-deoxoartemisinins, e.g. I, were proposed for synthesis. Several of the new compounds were synthesized employing the key synthetic intermediate II. In a second approach, the natural product (+)-artemisinic acid (III) was utilized as an acceptor for conjugate addition, and the resultant homologated acids were subjected to singlet oxygenation and acid treatment to provide artemisinin analogs. Under a new approach, we developed a one step reaction for the interconversion of artemisinin into artemisitene (IV) that did not employ selenium-based reagents and found that 2-arylethyliodides would undergo facile radical-induced conjugate addition to the exomethylene lactone of IV in good yield. The lactone carbonyls were removed sequentially by diisobutylaluminum hydride reduction followed directly by a second reduction (BF₃-etherate/Et₃SiH) to afford the desired corresponding pyrans. Six addnl. halogen-substituted aromatic side chains were installed via IV furnishing the bioassay candidates. The analogs were examined for in vitro antimalarial activity in the W-2 and D-6 clones of Plasmodium falciparum and were addnl. tested in vivo in Plasmodium berghei- and/or Plasmodium yoelii-infected mice. Several of the compounds emerged as highly potent orally active candidates without obvious toxicity. Of these, two were chosen for pharmacokinetic evaluation, V and VI. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3COA of Formula: 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. COA of Formula: C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nicotinamide Phosphoribosyltransferase Inhibitors, Design, Preparation, and Structure-Activity Relationship was written by Christensen, Mette K.;Erichsen, Kamille D.;Olesen, Uffe H.;Tjoernelund, Jette;Fristrup, Peter;Thougaard, Annemette;Nielsen, Soeren Jensby;Sehested, Maxwell;Jensen, Peter B.;Loza, Einars;Kalvinsh, Ivars;Garten, Antje;Kiess, Wieland;Bjorkling, Fredrik. And the article was included in Journal of Medicinal Chemistry in 2013.Quality Control of N-(5-Bromopentyl)phthalimide This article mentions the following:

Existing pharmacol. inhibitors for nicotinamide phosphoribosyltransferase (NAMPT) are promising therapeutics for treating cancer. By using medicinal and computational chem. methods, the structure-activity relationship for novel classes of NAMPT inhibitors is described, and the compounds are optimized. Compounds are designed inspired by the NAMPT inhibitor APO866 and cyanoguanidine inhibitor scaffolds. In comparison with recently published derivatives, the new analogs exhibit an equally potent antiproliferative activity in vitro and comparable activity in vivo. The best performing compounds from these series showed subnanomolar antiproliferative activity toward a series of cancer cell lines (compound 15: IC₅₀ 0.025 and 0.33 nM, in A2780 (ovarian carcinoma) and MCF-7 (breast), resp.) and potent antitumor in vivo activity in well-tolerated doses in a xenograft model. In an A2780 xenograft mouse model with large tumors (500 mm³), compound 15 reduced the tumor volume to one-fifth of the starting volume at a dose of 3 mg/kg administered i.p., bid, days 1-9. Thus, compounds found in this study compared favorably with compounds already in the clinic and warrant further investigation as promising lead mols. for the inhibition of NAMPT. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Quality Control of N-(5-Bromopentyl)phthalimide).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and biological evaluation of pyrazol-furan carboxamide analogues as novel Akt kinase inhibitors was written by Zhan, Wenhu;Xu, Lei;Dong, Xiaowu;Dong, Jun;Yi, Xiao;Ma, Xiaodong;Qiu, Ni;Li, Jia;Yang, Bo;Zhou, Yubo;Hu, Yongzhou. And the article was included in European Journal of Medicinal Chemistry in 2016.Recommanded Product: 1196-90-3 This article mentions the following:

A series of novel pyrazolylfuran carboxamides I (24a–d; X = S, R² = R³ = H; R¹, R⁴: a, H, 4-F; b, Cl, 4-F; c, Br, 4-F; d, H, 3,4-Cl₂; 25a–e, X = O, R³ = H, R¹, R², R⁴: a, Cl, H, 4-F; b, Br, H, 4-F; c, Br, H, 3,4-Cl₂; d, Cl, Cl, 4-F; e, Cl, Cl, 3,4-Cl₂; 27a–c, X = NMe, R¹, R², R³, R⁴: a, Br, H, H, 3,4-Cl₂; b, Br, Br, H, 3,4-Cl₂; c, Cl, Cl, Cl, 3,4-Cl₂) and II (26a–c; R¹, R², R⁴: a, H, Br, 3,4-Cl₂; b, Cl, Br, 3,4-Cl₂; c, Br, Br, 3,4-Cl₂) were designed, synthesized and biol. evaluated for their Akt1 inhibitory activities, as well as anti-proliferative efficacies against HCT116 and OVCAR-8 cell lines. Most compounds exhibited moderate to excellent Akt1 inhibitory activities, together with favorable cytotoxicities. Further kinase selectivity assay of the most promising compound 25e illustrated that it was also potent against the structurally related AGC kinases, including Akt2, Akt3, ROCK1 and PKA, but was specific over kinases from other subfamilies. In addition, the Western blot anal. indicated that 25e could significantly suppress the phosphorylation level of Akt substrate GSK3β in PC-3 cell. Moreover, 25e demonstrated a concentration-dependent inhibition of phosphorylation of PRAS40 in LNCaP cell, with IC₅₀ value of 30.4 nM. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3Recommanded Product: 1196-90-3).

Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Recommanded Product: 1196-90-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of Small-Molecule Sulfonamide Fluorescent Probes for GPR120 was written by Liu, Pan;Ma, Siyue;Yan, Chongzheng;Qin, Xiaojun;Zhao, Pei;Li, Qi;Cui, Yuanyuan;Li, Minyong;Du, Lupei. And the article was included in Analytical Chemistry (Washington, DC, United States) in 2019.Computed Properties of C13H14BrNO2 This article mentions the following:

GPR120 is a novel target for the treatment of metabolic disease and type 2 diabetes. The small-mol. fluorescent probe could help us locate GPR120 visually and guide in-depth study of GPR120. In this study, we synthesized six nonacidic sulfonamide fluorescent probes and tested their optical and biol. properties. Compared to previous probes for GPR120, these probes, with sulfonamide structure, have high selectivity on GPR120. We used these probes to establish a BRET binding assay system to screen agonists and antagonists of GPR120. It is expected that these novel fluorescent probes may become useful tools in studying pharmacol. and physiol. of GPR120. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Computed Properties of 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. 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.Computed Properties of C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lewis Basic Amine Catalyzed Aza-Michael Reaction of Indole- and Pyrrole-3-carbaldehydes was written by Xu, Chang-Jiang;Du, Wei;Albrecht, Lukasz;Chen, Ying-Chun. And the article was included in Synthesis in 2020.Recommanded Product: 881676-32-0 This article mentions the following:

3-Formyl substituted indoles or pyrroles can form HOMO-raised dearomative aza-dienamine-type intermediates with secondary amines, which can undergo direct aza-Michael addition to β-trifluoromethyl enones to afford N-alkylated products efficiently, albeit with low to fair enantioselectivity. In addition, similar asym. aza-Michael additions of these heteroarenes and crotonaldehyde are realized under dual catalysis of chiral amines, and the adducts are obtained with moderate to good enantioselectivity. In the experiment, the researchers used many compounds, for example, 5-Bromo-1H-pyrrole-3-carbaldehyde (cas: 881676-32-0Recommanded Product: 881676-32-0).

5-Bromo-1H-pyrrole-3-carbaldehyde (cas: 881676-32-0) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Recommanded Product: 881676-32-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Study of interactions between alcohol and amine functions. Thermolysis of hydroxides and salts of ω-(trialkylammonio)-1-alkanols was written by Barbry, Didier;Hasiak, Bruno. And the article was included in Collection of Czechoslovak Chemical Communications in 1983.Reference of 50592-87-5 This article mentions the following:

Products of the thermolysis of R₃N⁺(CH₂)_nOH.OH^– (I; R = Me, Et, Pr; n = 4-8) were identified. Major products were HO(CH₂)_n-2CH:CH₂ and HO(CH₂)_nR₂. Intramol. cyclization was only important for I (R = Me, n = 4; R = Pr, n = 5) giving 91.5% THF and 21.7% tetrahydropyran, resp. RO(CH₂)_n-2CH:CH₂ and RO(CH₂)_nNR₂ (R = Me, n = 6,7) were formed in 17.6-20.6% yields. Thermal decomposition of Me₃N⁺(CH₂)_nOH.OAc^– (n = 5, 6) gave 90.6% and 82.4% HO(CH₂)_nNMe₂ (n = 5, 6) and 5.6% and 16.0% AcO(CH₂)_nNMe₂ (n = 5, 6), resp. Pyrolysis of HO(CH₂)₆N⁺Me₃.Cl^– gave 82.4% HO(CH₂)₆NMe₂ and 8.2% HO(CH₂)₆Cl. In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Reference of 50592-87-5).

1-Bromo-6-methoxyhexane (cas: 50592-87-5) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Reference of 50592-87-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electron impact ionization mass spectra of 1,2,4-triazine derivatives with antimicrobial activity was written by Sherif, M. H.;Abd El-Hady, H.. And the article was included in Organic Chemistry: An Indian Journal in 2013.Reference of 108940-96-1 This article mentions the following:

2-(Aminothiocarbonyl)-3-aryl-5-arylidene-1,2,4-triazin-6-ones I (R = Cl, R¹ = R³ = R⁴ = H, R² = Br; R = Cl, R¹ = R³ = Br, R² = MeO, R⁴ = H; R = R¹ = R³ = R⁴ = H, R² = Cl) were prepared via condensation of 4-benzylidene-5-oxazolinones with thiosemicarbazide. The corresponding 1-methyl-3-thioxo-4-aryl-6-arylidenetriazolo[2,1-a][1,2,4]triazin-7-ones II were obtained by refluxing I with Ac₂O. Treatment of I with PhCOCl in AcOH yielded the corresponding 2-[(benzoylamino)thiocarbonyl]-3-aryl-5-arylidene-1,2,4-triazin-6-ones I (R⁴ = PhCO). The electron impact ionization mass spectra of I (R = Cl, R¹ = R³ = Br, R² = MeO, R⁴ = H; R = Cl, R¹ = R³ = H, R² = Br, R⁴ = PhCO; R = Cl, R¹ = R³ = Br, R² = MeO, R⁴ = PhCO) and II (R = Cl, R¹ = R³ = H, R² = Br; R = Cl, R¹ = R³ = Br, R² = MeO), showed a weak mol. ion peak and a base peak of m/z 139 resulting from a cleavage fragmentation, but I (R = Cl, R¹ = R³ = R⁴ = H, R² = Br) exhibited a base peak at m/z 138. Compounds I (R = R¹ = R³ = H, R² = Cl, R⁴ = H or PhCO) gave a characteristic fragmentation pattern with a very stable fragment at m/z 104, while II (R = R¹ = R³ = H, R² = Cl) gave m/z 119. Some of the compounds were screened for antifungal activity. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Reference of 108940-96-1).

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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Reference of 108940-96-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors was written by James, Clint A.;DeRoy, Patrick;Duplessis, Martin;Edwards, Paul J.;Halmos, Teddy;Minville, Joannie;Morency, Louis;Morin, Sebastien;Simoneau, Bruno;Tremblay, Martin;Bethell, Richard;Cordingley, Michael;Duan, Jianmin;Lamorte, Louie;Pelletier, Alex;Rajotte, Daniel;Salois, Patrick;Tremblay, Sonia;Sturino, Claudio F.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Recommanded Product: 4457-67-4 This article mentions the following:

A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in I as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor. Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogs not requiring a basic amine to achieve antiviral activity. Addnl. modifications at N-1 resulted in II which demonstrated excellent antiviral potency and improved physicochem. properties. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Recommanded Product: 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Recommanded Product: 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes was written by Shen, Wen-Bo;Tang, Xiang-Ting;Zhang, Ting-Ting;Lv, Dong-Can;Zhao, Dan;Su, Tong-Fu;Meng, Lei. And the article was included in Organic Letters in 2021.Safety of 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

An efficient copper(I)-catalyzed enyne R²CCN(R¹)CH₂C(R³)=CHR⁴ (R¹ = Ms, Ts, SO2Ph, Bs; R² = Ph, 3-bromophenyl, thiophen-3-yl, etc.; R³ = H, Me; R⁴ = H, Me, Ph, 4-chlorophenyl, etc.) and 2-(CH₂=CH)-R⁵C₆H₃C(O)CCR⁶ (R⁵ = H, Me, 5-F, etc.; R⁶ = Ph, 4-fluorophenyl, 4-methoxyphenyl) oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives I, II and III is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams I and II in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Safety of 2-Bromo-4-(trifluoromethyl)benzaldehyde).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and biological evaluation of novel T-type calcium channel blockers was written by Choi, Ja Youn;Seo, Han Na;Lee, Min Joo;Park, Seong Jun;Park, Sung Jun;Jeon, Ji Young;Kang, Joo Hi;Pae, Ae Nim;Rhim, Hyewhon;Lee, Jae Yeol. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Recommanded Product: N-(5-Bromopentyl)phthalimide This article mentions the following:

3,4-Dihydroquinazoline analogs, e.g., I, substituted by N-methyl-N-(5-pyrrolidinopentyl)amine at the 2-position were synthesized and their blocking effects were evaluated for T- and N-type calcium channels. I, compared to mibefradil (IC₅₀ = 1.34 ± 0.49 μM), was about 5-fold potent (IC₅₀ = 0.26 ± 0.01 μM) for T-type calcium channel (α_1G) blocking and its selectivity of T/N-type was also improved (7.5 vs. 1.4 of mibefradil). In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Recommanded Product: N-(5-Bromopentyl)phthalimide).

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.Recommanded Product: N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary