Category: bromides-buliding-blocks

Sun, Jufeng; Ambrus, Joey I.; Baker, Jennifer R.; Russell, Cecilia C.; Cossar, Peter J.; Sakoff, Jennette A.; Scarlett, Christopher J.; McCluskey, Adam published the artcile< 3,5-Bis(trifluoromethyl)phenylsulfonamides, a novel pancreatic cancer active lead. Investigation of the terminal aromatic moiety>, Reference of 3959-07-7, the main research area is pancreatic cancer anticancer agent virtual screening.

Virtual screening identified N-(6-((4-bromobenzyl)amino)hexyl)-3,5-bis(trifluoromethyl)benzenesulfonamide (1) a lead compound that bound to the S100A2-p53 binding groove. S100A2 is a Ca2+ binding protein with implications in cell signaling and is known to be upregulated in pancreatic cancer. It is a validated pancreatic cancer drug target. Lead 1, inhibited the growth of the MiaPaCa-2 pancreatic cancer cell line (GI50 = 2.97 μM). Focused compound libraries were developed to explore the SAR of this compound class with 4 libraries and 43 compounds total. Focused library (Library 1) development identified lipophillic sulfonamides as preferred for MiaPaCa-2 activity, with -CF3 and -C(CH3)3 substituents well tolerated (MiaPaCa-2 GI50 < 6 μM). Contraction of the hexylamino spacer to Et (Library 2) and Pr (Library 3) proved beneficial to activity against a broad spectrum panel of cancer cell lines: HT29 (lung), MCF-7 (breast), A2780 (ovarian), H460 (colon), A431 (skin), Du145 (prostate), BE2-C (neuroblastoma), U87 and SJ-G2 (glioblastoma) (cohort-1); and a pancreatic cancer cell line panel: MiaPaCa-2, BxPC-3, AsPC-1, Capan-2, HPAC and PANC-1 (cohort-2). With a marked preference for a Pr linker the observed GI50 values ranged from 1.4 to 30 μM against cohort-1 and 1.4-30 μM against cohort-2 cell lines. In Library 4 the terminal aromatic moiety was explored with 4-substituted analogs preferred (with activity of 48 (4-Cl) > 47 (3-Cl) > 46 (2-Cl)) against the cell lines examined The introduction of bulky aromatic moieties was well tolerated, e.g. dihydrobenzo[b][1,4]dioxine (51) returned cohort-2 GI50 values of 1.2-3.4 μM. In all instances the observed docked binding poses and binding scores were consistent with the observed cytotoxicity. This in turn supports, but does not prove, that these analogs function via S100A2-p53 binding groove inhibition.

Bioorganic & Medicinal Chemistry Letters published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Reference of 3959-07-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mitsudo, Koichi; Kobashi, Yoshiaki; Nakata, Kaito; Kurimoto, Yuji; Sato, Eisuke; Mandai, Hiroki; Suga, Seiji published the artcile< Cu-Catalyzed Dehydrogenative C-O Cyclization for the Synthesis of Furan-Fused Thienoacenes>, HPLC of Formula: 81107-97-3, the main research area is thiophenyl phenol copper catalyst dehydrogenative cyclization coupling; furan fused thienoacene preparation.

The first Cu-catalyzed dehydrogenative C-O cyclization for the synthesis of furan-fused thienoacenes is described. A variety of heteroacenes including a thieno[3,2-b]furan or a thieno[2,3-b]furan skeleton were synthesized by intramol. C-H/O-H coupling. The use of a mixed solvent of N-methyl-2-pyrrolidone, ethylene glycol monomethyl ether, and toluene was essential for suppressing side reactions and efficiently promoting the reaction. Double C-O cyclization was also conducted to afford highly π-expanded furan-fused thienoacenes.

Organic Letters published new progress about Bond cleavage. 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, HPLC of Formula: 81107-97-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mal, Abhijit; Wani, Imtiyaz Ahmad; Goswami, Gaurav; Ghorai, Manas K. published the artcile< Synthesis of Nonracemic 1,4-Benzoxazines via Ring Opening/Cyclization of Activated Aziridines with 2-Halophenols: Formal Synthesis of Levofloxacin>, Formula: C7H4BrF3O, the main research area is benzoxazine preparation; aziridine halophenol ring opening cyclization.

Novel 3,4-dihydro-1,4-benzoxazine derivatives have been synthesized by an efficient and simple method in excellent enantio- and diastereospecificity (ee > 99%, de > 99%). The reaction proceeds via Lewis acid-catalyzed SN2-type ring opening of activated aziridines with 2-halophenols followed by Cu(I)-catalyzed intramol. C-N cyclization in a stepwise fashion under one-pot conditions to furnish the 3,4-dihydro-1,4-benzoxazine derivatives in excellent yields (up to 95%). The strategy offers a short and efficient synthesis to (S)-3-methyl-1,4-benzoxazine (S)-3v, a late stage intermediate in the synthesis of levofloxacin.

Journal of Organic Chemistry published new progress about Aziridines Role: RCT (Reactant), RACT (Reactant or Reagent). 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, Formula: C7H4BrF3O.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xing, Qiaoyan; Xiao, Fuhong; Mao, Guojiang; Deng, Guo-Jun published the artcile< A Four-Component Reaction for the Synthesis of Thienopyrrolediones under Transition Metal Free Conditions>, Related Products of 188813-04-9, the main research area is thienopyrrole dione preparation green chem; aldehyde ketoamide multicomponent reaction.

A three-starting-material four-component reaction strategy is described to construct thienopyrrolediones (TPDs) I (R = H, Me, Et, Ph, Cy; R1 = Ph, naphthalen-2-yl, furan-2-yl, quinolin-8-yl, etc.; R2 = Ph, 4-(benzyloxy)phenyl, thiophen-2-yl, pyridin-3-yl, etc.) from the simplest raw materials, elemental sulfur, aldehydes R1CHO and R2CHO, and β-ketoamides e.g., 1-methylpyrrolidin-2-one, under transition metal free conditions. Compared with traditional multistep reaction sequences, this process is simple, efficient, environmentally friendly, and atom-economic and has laid the foundation for further development of an easily synthesized TPD unit.

Organic Letters published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Related Products of 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhao, Tian-Yuan; Xiao, Li-Jun; Zhou, Qi-Lin published the artcile< Nickel-Catalyzed Desymmetric Reductive Cyclization/Coupling of 1,6-Dienes: An Enantioselective Approach to Chiral Tertiary Alcohol>, Name: Methyl 2-bromo-4-methoxybenzoate, the main research area is chiral tertiary alc preparation enantioselective; diene desym reductive cyclization coupling nickel catalyst; 1,6-Dienes; Asymmetric Reductive Coupling; Desymmetric Catalysis; Nickel Catalysis; Tertiary Alcohols.

Authors have developed a nickel-catalyzed desym. reductive cyclization/coupling of 1,6-dienes. The reaction provides an efficient method for constructing a chiral tertiary alc. and a quaternary stereocenter by a single operation. The method has excellent diastereoselectivity and high enantioselectivity, a broad substrate scope, as well as good tolerance of functional groups. Preliminary mechanism studies show that alkyl nickel(I) species are involved in the reaction.

Angewandte Chemie, International Edition published new progress about Alkadienes Role: RCT (Reactant), RACT (Reactant or Reagent). 17100-65-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO3, Name: Methyl 2-bromo-4-methoxybenzoate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Suzaki, Yuji; Abe, Tomoko; Takei, Asami; Fukuchi, Yugo; Koizumi, Take-aki; Osakada, Kohtaro; Horie, Masaki published the artcile< Ferrocene-Containing Pseudorotaxanes in Crystals: Aromatic Interactions with Hammett Correlation>, Safety of 4-Bromobenzylamine, the main research area is ferrocene pseudorotaxane crystal structure aromatic interaction Hammett correlation; Hammett constants; aromatic interaction; crystal structure; pseudorotaxane.

Single crystals of pseudorotaxanes, [(FcCH2NH2CH2Ar)(DB24C8)][PF6] (DB24C8 = dibenzo[24]crown-8, Fc = Fe(C5H4)(C5H5), Ar = -C6H3-3,4-Cl2, -C6H3-3,4-F2, -C6H4-4-F, -C6H4-4-Cl, -C6H4-4-Br, -C6H3-3-F-4-Me, -C6H4-4-I) and [(FcCH2NH2CH2C6H4-4-Me)(DB24C8)][Ni(dmit)2] (dmit = 1,3-dithiole-2,4,5-dithiolate), were obtained from solutions containing DB24C8 and ferrocenylmethyl(arylmethyl)ammonium. X-ray crystallog. analyses of the pseudorotaxanes revealed that the aryl ring of the axle moiety and the catechol ring of the macrocyclic component were at close centroid distances and parallel or tilted orientation. The structures with parallel aromatic rings showed correlation of the distances between the centroids to Hammett substituent constants of the aryl groups.

Molecules published new progress about Aromatic compounds Role: PRP (Properties) (interaction). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Safety of 4-Bromobenzylamine.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Malysheva, Yulia B.; Combes, Sebastien; Fedorov, Alexey Yu.; Knochel, Paul; Gavryushin, Andrei E. published the artcile< New method of synthesis and biological evaluation of some combretastatin A-4 analogues>, Formula: C12H16BrNO2, the main research area is combretastatin A4 analog stereoselective preparation antitumor.

A series of novel combretastatin A-4 analogs was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50 = 0.022-10.31 μM).

Synlett published new progress about Antitumor agents. 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Formula: C12H16BrNO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Domaradzki, Maciej E.; Liu, Xiaochen; Ong, Jiye; Yu, Gyeongah; Zhang, Gan; Simantov, Ariel; Perl, Eliyahu; Chen, Yu published the artcile< Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate>, Quality Control of 17100-65-1, the main research area is isoquinolinone isochromenone preparation; alkynylarylester intramol cyclization triflic acid ammonium acetate.

A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Bronsted acid-mediated intramol. cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Bronsted acid induced intramol. cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.

Tetrahedron published new progress about Benzopyrans Role: SPN (Synthetic Preparation), PREP (Preparation) (isochromenones). 17100-65-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO3, Quality Control of 17100-65-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sinai, Adam; Simko, Daniel Cs.; Szabo, Fruzsina; Paczal, Attila; Gati, Tamas; Benyei, Attila; Novak, Zoltan; Kotschy, Andras published the artcile< Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application>, Safety of 2,4,6-Trimethylbromobenzene, the main research area is aryl diadamantyl phosphine ligand palladium catalyst preparation coupling; Buchwald Hartwig tosyl hydrazone coupling.

Synthesis, temperature-dependent NMR structure study and use of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In the authors’ study, the authors demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

European Journal of Organic Chemistry published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Safety of 2,4,6-Trimethylbromobenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fouque, Amelie; Delalande, Olivier; Jean, Mickael; Castellano, Remy; Josselin, Emmanuelle; Malleter, Marine; Shoji, Kenji F.; Hung, Mac Dinh; Rampanarivo, Hariniaina; Collette, Yves; Weghe, Pierre van de; Legembre, Patrick published the artcile< A Novel Covalent mTOR Inhibitor, DHM25, Shows in Vivo Antitumor Activity against Triple-Negative Breast Cancer Cells>, Electric Literature of 3893-18-3, the main research area is covalent mTOR inhibitor DHM25 antitumor breast cancer.

Constitutive activation of the PI3K/mTOR signaling pathway contributes to carcinogenesis and metastasis in most, if not all, breast cancers. From a chromene backbone reported to inhibit class I PI3K catalytic subunits, several rounds of chem. syntheses led to the generation of a new collection of chromologues that showed enhanced ability to kill PI3K-addicted cancer cells and to inhibit Akt phosphorylation at serine 473, a hallmark of PI3K/mTOR activation. This initial screen uncovered a chromene designated DHM25 that exerted potent antitumor activity against breast tumor cell lines. Strikingly, DHM25 was shown to be a selective and covalent inhibitor of mTOR using biochem. and cellular analyses, modeling, and a large panel of kinase activity assays spanning the human kinome (243 kinases). Finally, in vivo, this novel drug was an efficient inhibitor of growth and metastasis of triple-neg. breast cancer cells, paving the way for its clin. application in oncol.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Electric Literature of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary