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6-Quinoxalinecarboxylic acid, 2,3-bis(bromomethyl)- Sale

目录号 : GC34145

6-Quinoxalinecarboxylicacid,2,3-bis(bromomethyl)-是抗体偶联药物(ADC)的连接桥。

6-Quinoxalinecarboxylic acid, 2,3-bis(bromomethyl)- Chemical Structure

Cas No.:32602-11-2

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1mg
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5mg
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10mg
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25mg
¥2,250.00
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50mg
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100mg
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Sample solution is provided at 25 µL, 10mM.

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产品描述

6-Quinoxalinecarboxylic acid, 2,3-bis(bromomethyl)- is an useful linker for antibody-drug-conjugations (ADCs), extracted from [Bioorg Chem. 2012 Apr-Jun;41-42:1-5.] compound 1i.

[1]. Ishikawa H, et al. Synthesis and antimicrobial activity of 2,3-bis(bromomethyl)quinoxaline derivatives. Bioorg Chem. 2012 Apr-Jun;41-42:1-5.

Chemical Properties

Cas No. 32602-11-2 SDF
Canonical SMILES #214fKY3m4BAPgk3PgBJfzY3m4kxLiy3m4kxLiCbfCBJPgBAmgO=
分子式 C11H8Br2N2O2 分子量 360
溶解度 DMSO : ≥ 100 mg/mL (277.78 mM);Water : < 0.1 mg/mL (insoluble) 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
为了提高溶解度,请将管子加热至37℃,然后在超声波浴中震荡一段时间。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.7778 mL 13.8889 mL 27.7778 mL
5 mM 0.5556 mL 2.7778 mL 5.5556 mL
10 mM 0.2778 mL 1.3889 mL 2.7778 mL
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Research Update

Synthesis of a New Series of Nitrogen/Sulfur Heterocycles by Linking Four Rings: Indole; 1,2,4-Triazole; Pyridazine; and Quinoxaline

A new series of nitrogen and sulfur heterocyclic systems were efficiently synthesized by linking the following four rings: indole; 1,2,4-triazole; pyridazine; and quinoxaline hybrids. The strength of the acid that catalyzes the condensation of 4-amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 with aromatic aldehydes controlled the final product. Reflux in glacial acetic acid yielded Schiff bases 2-6, whereas concentrated HCl in ethanol resulted in a cyclization product at C-3 of the indole ring to create indolo-triazolo-pyridazinethiones 7-16. This fascinating cyclization approach was applicable with a wide range of aromatic aldehydes to create the target cyclized compounds in excellent yield. Additionally, the coupling of the new indolo-triazolo-pyridazinethiones 7-13 with 2,3-bis(bromomethyl)quinoxaline, as a linker in acetone and K2CO3, yielded 2,3-bis((5,6-dihydro-14H-indolo[2,3-d]-6-aryl-[1,2,4-triazolo][4,3-b]pyridazin-3 ylsulfanyl)methyl)quinoxalines 19-25 in a high yield. The formation of this new class of heterocyclic compounds in high yields warrants their use for further research. The new compounds were characterized using nuclear magnetic resonance (NMR) and mass spectral analysis. Compound 6 was further confirmed by the single crystal X-ray diffraction technique.

Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions

Conformationally constrained cyclic alpha-amino acid derivatives were synthesized under solid-liquid phase-transfer catalysis conditions. This methodology involves the bis-alkylation of ethyl isocyanoacetate with various alpha,alpha'-dibromo-o-xylene derivatives [alpha,alpha'-dibromo-o-xylene 5, 2,3-bis(bromomethyl)-1, 4-dimethoxybenzene 6, 1,2-bis(bromomethyl)-4,5-dibromobenzene 7, 2, 3-bis(bromomethyl)naphthalene 8, 1,8-bis(bromomethyl)-naphthalene 9, 6,7-bis(bromomethyl)-2,2-dimethyl-1H-phenalene-1,3(2H)-dione 10, 2, 3-bis(bromomethyl)-1,4-anthraquinone 11, 6, 7-bis(bromomethyl)quinoxaline 12, 3,4-bis(bromomethyl)furan 13, 1,2, 4,5-tetrakis(bromomethyl)benzene 28, and hexakis(bromomethyl)benzene 30] using potassium carbonate as a base and tetrabutylammonium hydrogensulfate as a phase-transfer catalyst to give corresponding isonitrile derivatives, which upon hydrolysis with HCl in ethanol gave amino esters. Using this method electron-deficient as well as electron-rich and halogen-substituted indan-based alpha-amino acids were prepared. The preparation of bis-indan as well as tris-indan alpha-amino esters is also described.

Synthesis and characterization of diiron dithiolate complexes containing a quinoxaline bridge

A potential model complex for the hydrogenase active site, [Fe(2){(μ-CH(2)S)(2)R}(CO)(6)] (1) (R = quinoxaline), was synthesized by condensation of [(μ-LiS)(2)Fe(2)(CO)(6)] with 2,3-bis(bromomethyl)quinoxaline. Reactions of 1 with bis(diphenylphosphino)methane (dppm) under a range of conditions yielded substituted complexes [Fe(2){(μ-CH(2)S)(2)R}(CO)(5)(dppm)] (2), [Fe(2){(μ-CH(2)S)(2)R}(CO)(4)(k(2)-dppm)] (3) and [Fe(2){(μ-CH(2)S)(2)R}(CO)(4)(μ-dppm)] (4). X-ray crystallography confirms that in 2, the dppm is terminally bonded to an iron atom via one phosphorus atom, whereas in 3, it acts as a chelating ligand to coordinate to an iron center in a dibasal-substituted manner. In 4, the dppm bridges the two iron atoms in a cis basal/basal fashion with one phosphorus bonded to each iron atom. Treatment of 1 with various tertiary phosphines at room temperature in acetonitrile (MeCN) generates a range of mono-substituted products [Fe(2){(μ-CH(2)S)(2)R}(CO)(5)L] (5, L = PEt(3); 6, PMe(3); 7, PPh(3); 8, Me(2)PPh). With Bu(t)NC, mono- and di-substituted [Fe(2){(μ-CH(2)S)(2)R}(CO)(5)(Bu(t)NC)] (9) and [Fe(2){(μ-CH(2)S)(2)R}(CO)(4)(Bu(t)NC)(2)] (10) complexes are generated. All the complexes were characterized by elemental analysis, IR, MS and NMR spectroscopy. IR and NMR spectroscopic studies suggest that addition of excess HBF(4)·OEt(2) acid to 1-4 led to the protonation of quinoxaline nitrogen atoms. In contrast, 5-10 were not stable in acidic media. Electrochemistry of 1-4 was investigated in the acetonitrile medium (0.1 M Bu(4)NPF(6)). The electrochemical instability of the reduced ligand, quinoxaline, and the reduced forms of these complexes revealed from the electrochemical studies suggests that they do not provide ideal models of the hydrogenase active site.

Peroxiredoxin-1 from the human hookworm Ancylostoma ceylanicum forms a stable oxidized decamer and is covalently inhibited by conoidin A

Hookworms are parasitic nematodes that have a devastating impact on global health, particularly in developing countries. We report a biochemical and structural analysis of a peroxiredoxin from the hookworm Ancylostoma ceylanicum, AcePrx-1. Peroxiredoxins provide antioxidant protection and act as signaling molecules and chaperones. AcePrx-1 is expressed in adult hookworms and can be inactivated by 2,3-bis(bromomethyl)quinoxaline-1,4-dioxide (conoidin A). Conoidin A inactivates AcePrx-1 by alkylating or crosslinking the catalytic cysteines, while maintaining the enzyme in the "locally unfolded" conformation. Irreversible oxidation of the resolving cysteine may contribute additional inhibitory activity. A crystal structure of oxidized AcePrx-1 reveals a disulfide-linked decamer. A helix macrodipole near the active site increases the reactivity of the catalytic cysteines to conoidin A. This work demonstrates the promise of conoidin compounds as probes to evaluate peroxiredoxins as drug targets in human parasites.