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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 16588-26-4, is researched, Molecular C6H3BrClNO2, about Efficient and recyclable bimetallic Co-Cu catalysts for selective hydrogenation of halogenated nitroarenes, the main research direction is nitroarene selective hydrogenation cobalt copper recyclable catalyst.Synthetic Route of C6H3BrClNO2.

Silica supported N-doped carbon layers encapsulating Co-Cu nanoparticles (Co1Cux@CN/SiO2) were prepared by a one-step impregnation of Co(NO3)2·6H2O, Cu(NO3)2·3H2O, urea and glucose, following in situ carbothermal reduction Effects of Cu contents on the catalytic performance of the Co1Cux@CN/SiO2 catalysts were investigated for selective hydrogenation of p-chloronitrobenzene to p-chloroaniline. The Co1Cu0.30@CN/SiO2 with Cu/Co molar ratio of 0.30:1 presented much higher activity and stability than the monometallic Co@CN/SiO2 catalyst. The addition of Cu into Co1Cux@CN/SiO2 catalysts had favorable effects on the formation of highly active Co-N sites and N-doped carbon layer. The role of the N-doped carbon layer was to protect the Co from oxidation by air, and the Co1Cu0.30@CN/SiO2 could be reused for at least 12 cycles without decrease in catalytic efficiency. Mechanistic and in situ IR studies revealed that the interaction effect between the Co and Cu atoms made the surface of Co highly electron rich, which decreased adsorption of halogen groups and resulting in the enhanced selectivity during chemoselective hydrogenation of halogenated nitroarenes for a wide scope of substrates.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Ohkanda, Junko; Lockman, Jeffrey W.; Kothare, Mohit A.; Qian, Yimin; Blaskovich, Michelle A.; Sebti, Said M.; Hamilton, Andrew D. researched the compound: 3-Bromo-4-chloronitrobenzene( cas:16588-26-4 ).Safety of 3-Bromo-4-chloronitrobenzene.They published the article 《Design and Synthesis of Potent Nonpeptidic Farnesyltransferase Inhibitors Based on a Terphenyl Scaffold》 about this compound( cas:16588-26-4 ) in Journal of Medicinal Chemistry. Keywords: terphenylcarboxylate aminomercaptopropylamino imidazolylmethylamino preparation farnesyl transferase inhibitor. We’ll tell you more about this compound (cas:16588-26-4).

By modification of key carboxylate, hydrophobic, and zinc-binding groups projected from a sterically restricted terphenyl scaffold, a series of simple and nonpeptide mimetics of the Cys-Val-Ile-Met tetrapeptide substrate of protein farnesyltransferase (FTase) have been designed and synthesized. A crystal structure of 4-nitro-2-phenyl-3′-methoxycarbonylbiphenyl shows that the terphenyl fragment provides a large hydrophobic surface that potentially mimics the hydrophobic side chains of the three terminal residues in the tetrapeptide. 2-Phenyl-3-{N-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]methyl}amino-3′-carboxylbiphenyl, in which the free thiol group was replaced with a 1-(4-cyanobenzyl)imidazole group, shows submicromolar inhibition activity against FTase in vitro and inhibits H-Ras processing in whole cells.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《o-Halogenated p-nitroaniline and its derivatives》. Authors are Korner, G.; Contardi.The article about the compound:3-Bromo-4-chloronitrobenzenecas:16588-26-4,SMILESS:BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl).Safety of 3-Bromo-4-chloronitrobenzene. Through the article, more information about this compound (cas:16588-26-4) is conveyed.

When p-NO2C6H4NH2 is dissolved or suspended in HCl and Cl or Br added a mixture, difficult to sep., of mono- and dihalogenated anilines with the halogen in the o-position is formed. If, however, gaseous Cl (mol. ratio 1 : 1) is passed into the b. HCl solution 2,4-Cl(O2N)C6H3NH2 is almost the sole product. This derivative mixed with some di-Cl derivative is obtained on chlorinating at -o°(Casella & Co., Ger. Pat., 109,189). At room temperature, on adding Cl slowly to the HCl solution, the di-Cl deriv, + quinone are formed. Chlorinating by Noelting’s method, using Ca(ClO)2, gave mixtures Similar results were obtained with Br. These derivatives are obtained by warming 1-nitro-3,4-dibromo (or dichloro) benzene with alc. NH3 in the scaled tube at 190°. The NH2 group substitutes p to NO2. By halogenating these monohalogen derivatives it is possible to get derivatives with 2 different halogens in the same ring. The action of ClI on a glac. AcOH solution of p-NO2C6H4NH2 gives mixtures from which the mono- and di-I derivatives can be separated by EtOH. 1-Nitro-3-chloro-4-aniline, bright yellow needles from hot H2O, m. 104.5°; acetyl derivative, straw-yellow flat prisms from EtOH, m. 139°. Diazotizing in H2SO4 or HNO3 suspension with gaseous HNO2 gives the diazo compound which, by way of the perbromide, goes into 1-nitro-3-chloro-4-bromobenzene, prisms from CHCl2, m. 62°. 1-Nitro-3-chloro-4-iodobenzene, almost colorless needles from EtOH, m. 103°, is obtained similarly, by way of the periodide. 1-Nitro-3-bromo-4-aniline, bright yellow needles, m. 104.5°, which with Ac2O gives the monoacetyl derivative, flat prisms, m. 114°, and the diacetyl derivative, short fat prisms, m. 132°. also from the mono derivative, by the action of Ac2O + traces of POCl3. Diazotizing and halogenating as above gives 1-nitro-3-bromo-4-chlorobenzene, white or colorless prisms, volatil with steam, m. 61°, is identical with the compound similarly obtained from 2,5-Cl(O2N)C6H3NH2. 1-Nitro-3-bromo-4-iodobenzene, prisms from AcOEt, m. 106°, was obtained similarly. 1-Nitro-3-iodo-4-aniline presents 2 forms: (1) stable yellow-red prisms, and (2) the labile forms golden yellow plates in C6H6, below 17°, m. 109°; monoacetyl derivative, bright yellow prisms; diacetyl derivative, more soluble than the mono compound, white needles. The diazo compound, on adding Cl, gives 1-nitro-3-iodo-4-chlorobenzene, needles, m. 78°, identical with the compound obtained similarly with I from 2,5-Cl(O2N)C6H2NH2. 1-Nitro-3,5-dichloro-4-aniline, yellow shining needles, m. 195°, slightly soluble in dilute and concentrate inorganic acids, unchanged by fuming HNO3 in the cold. To diazotize suspend in HNO3 (d. 1.38) and add gaseous HNO2 at o°; on diluting the explosive diazonium nitrate seps., fairly soluble in H2O. Ac2O + traces of POCl3 give the monoacetyl derivative, almost colorless needles, m. 215°, and the diacetyl derivative, monoclinic (Artini, Rend. ist. lombardo sci. lett., [2] 45, 1912), prisms, m. 142.5°, d. 1.565, more soluble than the mono compound In absolute EtOH + some concentrate H2SO4 + EtONO it gives 1-nitro-3,5-dichlorobenzene, plates, m. 65.4°, which on reducing with Sn + HCl gives 3,5-dichloroaniline, needles, m. 51.5°. The latter, by replacing NH3 with Cl, gives 1,3,4-trichlorobenzene, white needles, to. 63.5°, which is also obtained from 2,4,6-Cl3C8H2NH2, m. 77.5°, by replacing NH3, with H. 3,5-Cl2C4H3NH2 by replacing NH2 with Br gave 1-bromo-3,5-dichlorobenzene, needles, m. 75.8°. 1-Iodo-3,5-dichlorobenzene, m. 54°, was obtained similarly and is identical with that prepared similarly from 2,4,6-ICl2C6H2NH2, m. 84°. Anilines containing 3 identical halogen ats. in the 2,4,6-positions may be obtained by direct halogenation of PhNH2 of which they are the end products. The mixed halogenated anilines are made from anilines halogenated in p-position by adding two halogens (Br or ClI) in the o-position in glac. AcOH. o,p- or o,o-dihalogenanilines may even be used, but displacing of weak halogens may take place. All of the theoretically possible trihalogenbenzenes can be obtained by thus substituting halogen for NH2 in anilines. 2,6,4-Cl2(O2N)C6H2NH2 gives 1-nitro-3,4,5-trichlorobenzene, bright yellow prisms, m. 72.5°, volatil with steam; reduction and elimination of NH2 gives 1,2,3-C6H2Cl3, identical with that from 2,6-Cl2C6H3NH2 by the same method. 1-Nitro-3,5-dichloro-4-bromobenzene, from the above aniline, yellow. prisms, m. 88°, volatile with steam; similarly 1-nitro-3,5-dichloro-4-iodobenzene, yellow prisms, m. 154.8°, less volatile; reduction, etc., gives 1,3-dichloro-2-iodobenzene, thin plates, m. 68°, volatile with steam, also from 3,6-C;2C4H3NH2 with I. p-NO3 C4H4NH2 + Br gives 1-nitro-3,5-dibromo-4-aniline, yellow plates, m. 202.5°; Ac2O as above gives the monoacetyl derivative, colorless needles or triclinic prisms, isomorphous with the di-Cl compound, and the diacetyl derivative, prisms, m. 136°, triclinic pinacoidal, a : b : c = 1.0901 : 1 : 0.8325, a = 88° 43′ 4”. β = 70° 49′ 34”. γ = 93° 25′ 39”, d. 1.939.3 Diazotizing the above or 2,4.6-Br2(O2N)C5H2NH3 with EtONO, etc., gives 1-nitro-3,5-dibromobenzene, almost colorless needles, m. 104.5°; on reduction with Sn + HCl, etc., it gives sym.-dibromochlorobenzene, m. 119°, with Cl, or dibromoiodobenzene, m. 124.8°, with 1. Both are easily volatil with steam and may be prepared from the corresponding anilines and the latter also from 2,4,6-IBr2C6H2NH2. 1-Nitro-3,4,5-tribromobenzene, from the o,o-dibromoaniline by replacing NH3 with Br, yellowish prisms, m. 111.9° on reduction, etc., gives 1,2,3-C6H3Br3, m. 87.8°. 1-Nitro-3,5-dibromo-4-chlorobenzene from the same aniline, yellowish prisms, m. 92-7°, on reduction, etc., gives 2,6-Br2C6H3Cl, m. 71°, identical with the compound similarly obtained from 2,6-Br2C6H3NH2 by replacing NH2 with Cl. 1-Nitro-3,5-dibromo-4-iodobenzene, from 2,6,4-Br2(O2N)C6H2NH2, prisms, 135.5°, cannot be reduced to the aniline. The 2,6-Br2C6H2I was obtained from 2,6-Br2C6H3NH2, prisms, m. 72°. 1-Nitro-3,5-diiodo-4-aniline, from p-NO2C6H4NH2 + ClI in AcOH, yellow needles; m. 245°; monoacetyl derivative, yellow needles, m. 249°; diacetyl derivative, paler yellow prisms, m. 171°, triclinic pinacoidal, a : b : c = 0.9682 : 1 : O.7260, α = 83° 6’43”, β = 76°8’29”, γ = 99° 42′ 44”, d. 2.290. 1-Nitro-3,5-diiodobenzene, from the preceding, difficultly volatile with steam, yellowish prisms, m. 104.5°, on reducing with FeSO4 + NH3 gives 3,5-I2C6H2NH3, needles, m. 110°. 2,6,4-I2ClC6H2NH2 gave 1,3-diiodo-5-chlorobenzene, needles, m. 101°, discolors brown in the light. Similarly the 5-bromoaniline gave 1,3-diiodo-5-bromobenzene, m. 140°, slightly volatile with steam. 1,3,5-Triiodobenzene, from 2,4,6-I2C6H2NH2 or 3.5-I2C6H3NH2, opaque needle, m. 184.2°. Decompose of 2,6,4-I2(O2N)C6H2N2NO3 with b. aqueous Cu2Cl2 gave 1-nitro-3,5-diiodo-4-chlorobenzene, needles, m. 110°; reduction with FeSO4 + NH3 gives a poor yield, (NH4)2S gives a better yield of the aniline together with some S-containing compound The aniline gives 2,6-I2C6H3Cl, rhombic plates, m. 82°. 2,6,4-I2(O2N)(C6H2NH2 gives 1-nitro-3,5-diiodo-4-bromobenzene, white needles from EtOH, yellow prisms from CHCl3 m. 125.4°, and 1-nitro-3,4,5-triiodobenzene, yellow prisms from EtOH, contain C6H6 of crystallization when crystallized from C6H6; reduction with FeSO4 + NH3 gives 3,4,5-triiodoaniline with difficulty; (NH4)2S gives sym.-I2C6H2NH2. The I2C6H2NH2 gives 1,2,3-C6H2I2 on changing NH2 for H, m. 116°, which is identical with that from 2,3-I2C6H3NH2. 2,4-Cl(O2N)C6H3NH2 + Br gives 1-nitro-3-chloro-5-bromo-4-aniline, bright Yellow needles, m. 177.4°; monoacetyl derivative, straw-yellow needles, m. 224°; diacetyl derivative, prisms or plates, m. 139°, monoclinic, prismatic, a : b : c = 1.1127 : 1 : 0.8509, β = 70-36°, d. 1-749. 1-Nitro-3-chloro-5-bromobenzene, from the above aniline, plates, m. 81.2°. and this on reducing with Sn + HCl, etc., gives 3-chloro-5-bromoaniline, needles, or prisms. The latter, as well as 2,4,6-BrClIC6H2NH2, m. 110.5°, gives 1-chloro-3-bromo-5-iodobenzene, needles, m. 85.8°. 1-Nitro-3,4-dichloro-5-bromobenzene, yellowish prisms, m. 82.5°, 1-Nitro-3,4-dibromo-5-chlorobenzene, yellowish prisms, m. 99.5°, and 1-nitro-3-chloro-4-iodo-5 bromobenzene, needles, 159°, by replacing NH2 with a halogen in the preceding nitroaniline. 1,2-Dibromo-3-chlorobenzene, by reducing 3,4,5-Br2ClC6H2NO2, rhombic plates. m. 72.6°. 2,4-Cl(O2N)C6H2NH22, in HOAc + ClI gives 1-nitro-3-chloro-5-iodo-4-aniline, bright yellow needles, 195°; monoacetyl derivative, white prisms, m. 207°; diacetyl derivative, prisms, m. 113°, monoclinic, a : b : c = 1.038 :-1 : 0.799, β = 71.44°, d. 1.913. This aniline gives 1-nitro-3-chloro-5-iodobenzene, yellow prisms, m. 70.4° by replacing NH2 with Cl. 1-Nitro-3,4-dichloro-5-iodobenzene, from the aniline with Cl, bright yellow prisms, m. 59°, is not easily reduced by FeSO4 + NH3, but Sn + HCl gives 3,5-CHC6H3NH2, plates, m. 69.8°; with Br the aniline gives 1-nitro-3-chloro-4-bromo-5-iodobenzene, almost colorless needles, m. 95°; and with I it gives 1-nitro-3-chloro-4,5-diiodobenzene, almost colorless needles, m. 146.5°. 3,4,5-Cl2IC6H2NO2 + (NH4)2S in EtOH gives 3,4-Cl2C6H3NH2. 2,4-Br(O2N)C6H3NH2 + CH in HOAc gives 1-nitro-3-bromo-5-iodo-4-aniline, needles, m. 221°; monoacetyl derivative, yellowish prisms, m. 226°; diacetyl derivative, prisms, m. 134°, triclinic pinacoidal, a : b : C = 0.9470 : 1 : 0.7288, α = 83° 59′ 54”, β = 77° 30′ 18”, γ = 99° 6′ 14”, d.2.112. 1-Nitro-3-bromo-5-iodobenzene, by replacing NH2 with H in the preceding aniline, needles, m. 97.5°; 1-nitro-3-bromo-4-chloro-5-iodobenzene, by replacing NH2 with Cl, yellowish prisms or colorless needles, m. 84°.

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HPLC of Formula: 16588-26-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Optimization of Potent ATAD2 and CECR2 Bromodomain Inhibitors with an Atypical Binding Mode. Author is Lucas, Simon C. C.; Atkinson, Stephen J.; Bamborough, Paul; Barnett, Heather; Chung, Chun-wa; Gordon, Laurie; Mitchell, Darren J.; Phillipou, Alexander; Prinjha, Rab K.; Sheppard, Robert J.; Tomkinson, Nicholas C. O.; Watson, Robert J.; Demont, Emmanuel H..

Most bromodomain inhibitors mimic the interactions of the natural acetylated lysine (KAc) histone substrate through key interactions with conserved asparagine and tyrosine residues within the binding pocket. Herein we report the optimization of a series of Ph sulfonamides that exhibit a novel mode of binding to non-bromodomain and extra terminal domain (non-BET) bromodomains through displacement of a normally conserved network of four water mols. Starting from an initial hit mol., we report its divergent optimization toward the ATPase family AAA domain containing 2 (ATAD2) and cat eye syndrome chromosome region, candidate 2 (CECR2) domains. This work concludes with the identification of (R)-55 (GSK232)(I), a highly selective, cellularly penetrant CECR2 inhibitor with excellent physicochem. properties.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Sheng, Yao; Wang, Xueguang; Yue, Shengnan; Cheng, Gonglin; Zou, Xiujing; Lu, Xionggang researched the compound: 3-Bromo-4-chloronitrobenzene( cas:16588-26-4 ).Computed Properties of C6H3BrClNO2.They published the article 《In Situ Synthesized Silica-Supported Co@N-Doped Carbon as Highly Efficient and Reusable Catalysts for Selective Reduction of Halogenated Nitroaromatics》 about this compound( cas:16588-26-4 ) in ChemCatChem. Keywords: aromatic amine preparation chemoselective; nitrobenzene reduction cobalt catalyst. We’ll tell you more about this compound (cas:16588-26-4).

Silica-supported Co@N-doped carbon (Co@CN/SiO2) catalysts were first prepared by a one-step impregnation with a mixed solution of cobalt nitrate, glucose and urea, followed by in situ carbonization and reduction The Co@CN/SiO2 catalysts were investigated for the selective reduction of nitro aromatics RNO2 (R = Ph, 4,5-dichloro-2-nitroaniline, 2-chloro-3-nitropyridine, etc.) to the corresponding anilines RNH2 using hydrazine hydrate. The Co@CN/SiO2-500 carbonized at 500°C exhibited the highest catalytic activity and excellent stability without any decay of activity after 6 cycles for the reduction of nitrobenzene. Both metallic Co atoms and Co-N species formed in the Co@CN/SiO2 catalysts were active, but the Co-N species were dominant active sites. The high activities of the Co@CN/SiO2 catalysts were attributed to the synergistic effect between the Co and N atoms, promoting heterolytic cleavage of hydrazine to form H+/H- pairs. Representative examples demonstrated that the Co@CN/SiO2-500 could completely transform various halogen-substituted nitro aromatics to the corresponding halogenated anilines with high TOFs and selectivity of >99.5%.

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Product Details of 16588-26-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about L-(-)-Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles. Author is Zhou, Qifan; Du, Fangyu; Chen, Yuanguang; Fu, Yang; Sun, Wenjiao; Wu, Ying; Chen, Guoliang.

L-(-)-Quebrachitol (QCT) was found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.

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HPLC of Formula: 16588-26-4. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions. Author is Fu, Zhengjiang; Jiang, Ligao; Zuo, Qianming; Li, Zhaojie; Liu, Yanzhu; Wei, Zhenhong; Cai, Hu.

A series of aryl halides RX [R = 2-O2NC6H4, 2-NO2-4-MeOC6H3, 3-chlorothiophen-2-yl, etc.; X = Cl, Br, I] was synthesized via Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids using sodium halides as halogen donor under aerobic conditions was reported. The halodecarboxylation was shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib was performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicated that Cu plays a vital role and a radical pathway was involved in the transformation.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Optimization of 5-(2,6-dichlorophenyl)-3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase, the main research direction is dichlorophenylhydroxymercaptocyclohexenone inhibitor preparation lactate dehydrogenase isoenzyme LDHA crystal structure.Category: alcohols-buliding-blocks.

Optimization of 5-(2,6-dichlorophenyl)-3-hydroxy-2-mercaptocyclohex-2-enone using structure-based design strategies resulted in inhibitors with considerable improvement in biochem. potency against human lactate dehydrogenase A (LDHA). These potent inhibitors were typically selective for LDHA over LDHB isoform (4-10 fold) and other structurally related malate dehydrogenases, MDH1 and MDH2 (>500 fold). An X-ray crystal structure of enzymically most potent mol. bound to LDHA revealed two addnl. interactions associated with enhanced biochem. potency.

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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Nature Communications called Structural basis for itraconazole-mediated NPC1 inhibition, Author is Long, Tao; Qi, Xiaofeng; Hassan, Abdirahman; Liang, Qiren; De Brabander, Jef K.; Li, Xiaochun, which mentions a compound: 16588-26-4, SMILESS is BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl, Molecular C6H3BrClNO2, Quality Control of 3-Bromo-4-chloronitrobenzene.

Niemann-Pick C1, a lysosomal protein of 13 transmembrane helixes and three lumenal domains, exports low-d.-lipoprotein-derived cholesterol from lysosomes. TMs 3-7 of NPC1 comprise the sterol-sensing domain. Previous studies suggest that mutation of the NPC1-SSD or the addition of the anti-fungal drug itraconazole abolishes NPC1 activity in cells. However, the itraconazole binding site and the mechanism of NPC1-mediated cholesterol transport remain unknown. Here, we report a cryo-EM structure of human NPC1 bound to itraconazole, which reveals how this binding site in the center of NPC1 blocks a putative lumenal tunnel linked to the SSD. Functional assays confirm that blocking this tunnel abolishes NPC1-mediated cholesterol egress. Intriguingly, the palmitate anchor of Hedgehog occupies a similar site in the homologous tunnel of Patched, suggesting a conserved mechanism for sterol transport in this family of proteins and establishing a central function of their SSDs.

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Synthetic Route of C12H13BrN2O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: tert-Butyl 5-bromo-1H-indazole-1-carboxylate, is researched, Molecular C12H13BrN2O2, CAS is 651780-02-8, about The application of nitrogen heterocycles in mitochondrial-targeting fluorescent markers with neutral skeletons. Author is Wang, Yue; Xu, Bing; Sun, Ru; Xu, Yu-Jie; Ge, Jian-Feng.

Four different neutral fluorescent markers containing nitrogen heterocycles (quinoxaline, 1H-pyrazolo[3,4-b]pyridine, 1H-indazole and 1H-pyrrolo[2,3-b]pyridine) as targeting groups were designed and prepared in order to screen out structural units for targeting mitochondria. Several classical fluorophores (coumarin, 1,8-naphthalimide and Nile Red) were connected with these heterocycles via Suzuki coupling reactions. The derivatives of coumarin (dyes 1a and 2a-c) and 1,8-naphthalimide (dyes 3a-c) fluoresced in the blue-green region, while the Nile Red derivatives (dyes 1b and 4a-c) fluoresced in the red light region. The optical properties of the classical fluorophores, such as emission properties and photostability, were retained in the new dyes. All of them showed low cytotoxicity. Confocal fluorescence experiments in L929 normal cells and HeLa cancer cells indicated that dyes 1a-b targeted dual sites of mitochondria and lipid droplets. Moreover, dyes 2a-c, 3a-c and 4a-c targeted mitochondria; meanwhile, there are only a few mitochondria-targeting markers with neutral skeletons. Furthermore, it was found that nitrogen heterocycles with N-H bonds can improve the mitochondrial targeting ability of partial neutral fluorophores.

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