Tag: 200-300

The Mechanism of the ortho-Methylation of Nitrobenzenes by Dimethylsulfonium Methylide was written by Haiss, Peter;Zeller, Klaus-Peter. And the article was included in European Journal of Organic Chemistry in 2011.Related Products of 725266-66-0 The following contents are mentioned in the article:

Nitrobenzenes carrying an ortho substituent are selectively methylated at the free ortho position by reaction with dimethylsulfonium methylide. The importance of the ortho substituent is demonstrated by the failure of the methylation of nitrobenzene and 3- and 4-nitroanisole. This is explained by the out-of-plane geometry of the nitro group in the ortho-substituted derivative, which enables a specific interaction between the ylide and the nitro group favorable for attack of the methylide C atom at the neighboring free ortho position. As shown by appropriate deuterium-labeling studies, the addition is followed by an E1-like β-elimination with displacement of di-Me sulfide and subsequent protonation of the elimination product. This study involved multiple reactions and reactants, such as 1-Iodo-3-methoxy-2-nitrobenzene (cas: 725266-66-0Related Products of 725266-66-0).

1-Iodo-3-methoxy-2-nitrobenzene (cas: 725266-66-0) belongs to iodide derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Related Products of 725266-66-0

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

[¹²⁵I]-N-[(3-Azido-5-iodo)benzyl]dantrolene and [¹²⁵I]-N-{[3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl}dantrolene: photoaffinity probes specific for the physiological Ca²⁺ release from sarcoplasmic reticulum of skeletal muscle was written by Hosoya, Takamitsu;Aoyama, Hiroshi;Ikemoto, Takaaki;Hiramatsu, Toshiyuki;Kihara, Yasutaka;Endo, Makoto;Suzuki, Masaaki. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.SDS of cas: 368435-46-5 The following contents are mentioned in the article:

To capture and identify key mols. that regulate the release of Ca²⁺ from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, resp., at the hydantoin moiety were found to have a highly selective inhibitory effect on physiol. Ca²⁺ release (PCR) without affecting Ca²⁺-induced Ca²⁺ release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [¹²⁵I]GIF-0082 and [¹²⁵I]GIF-0276, which were synthesized by substituting a stannyl group with ¹²⁵I in the corresponding phenylstannane precursors. This study involved multiple reactions and reactants, such as (3-Amino-5-iodophenyl)methanol (cas: 368435-46-5SDS of cas: 368435-46-5).

(3-Amino-5-iodophenyl)methanol (cas: 368435-46-5) belongs to iodide derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.SDS of cas: 368435-46-5

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Metabolically stable diphenylamine derivatives suppress androgen receptor and BET protein in prostate cancer was written by Yu, Jiang;Zhou, Peiting;Du, Wu;Xu, Ruixue;Yan, Guoyi;Deng, Yufang;Li, Xinghai;Chen, Yuanwei. And the article was included in Biochemical Pharmacology (Amsterdam, Netherlands) in 2020.Application In Synthesis of 2-Chloro-4-iodobenzonitrile The following contents are mentioned in the article:

Androgen receptor (AR) is a crucial driver of prostate cancer (PC). AR-relevant resistance remains a major challenge in castration-resistant prostate cancer (CRPC). Bromodomain and extra-terminal domain (BET) family are critical AR coregulators. Here, we developed several diphenylamine derivatives and identified compound 7d that disrupted the functions of AR and BET family in prostate cancer and exhibited favorable metabolic stability in vitro and high drug exposure in vivo. We showed 7d not only bound to AR, suppressed transactivation of wild-type AR (wt-AR) and the mutant that mediates Enzalutamide resistance, but also reduced c-Myc protein expression through BET inhibition. In addition, 7d inhibited the proliferation of AR-pos. PC cells with favorable selectivity and suppressed AR-V7-expressing VCaP and 22Rv1 xenografts growth in vivo. Collectively, these results indicate the potential of lead compound 7d as an orally available AR and BET inhibitor to treat CRPC and overcome antiandrogen resistance. This study involved multiple reactions and reactants, such as 2-Chloro-4-iodobenzonitrile (cas: 371764-70-4Application In Synthesis of 2-Chloro-4-iodobenzonitrile).

2-Chloro-4-iodobenzonitrile (cas: 371764-70-4) belongs to iodide derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 2-Chloro-4-iodobenzonitrile

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Catalyst free hydrazone ligation for protein labeling and modification using electron-deficient benzaldehyde reagents was written by Xu, Yang;Wang, Yu;Liu, Peiyuan;Chu, Guo-Chao;Xu, Huajian;Li, Yi-Ming;Wang, Jun;Shi, Jing. And the article was included in Organic & Biomolecular Chemistry in 2018.Product Details of 371764-70-4 The following contents are mentioned in the article:

Bioorthogonal reactions have emerged as valuable tools for site-specific protein labeling and modification in vitro and in vivo. Hydrazone and oxime ligation has recently attracted considerable attention for wide applications in the conjugation of biomols. However, this kind of reaction has suffered from slow kinetics under physiol. conditions and toxicity or complications of the reaction system due to catalysts. The authors have developed an electron-deficient benzaldehyde reagent, which can be easily equipped with various types of bio-functional mols. for catalyst-free hydrazone ligation. The reagent can be equipped with not only small mols. such as fluorescence dyes or drugs, but also macromols. like PEG. These can be precisely ligated to the C-terminus of proteins by an efficient hydrazone reaction at neutral pH and room temperature The new reagent based catalyst-free hydrazone ligation provides a practical approach for the site specific modification of proteins. This study involved multiple reactions and reactants, such as 2-Chloro-4-iodobenzonitrile (cas: 371764-70-4Product Details of 371764-70-4).

2-Chloro-4-iodobenzonitrile (cas: 371764-70-4) belongs to iodide derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 371764-70-4

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Identification of a Novel Aminotetralin Class of HDAC6 and HDAC8 Selective Inhibitors was written by Tang, Guozhi;Wong, Jason C.;Zhang, Weixing;Wang, Zhanguo;Zhang, Nan;Peng, Zhenghong;Zhang, Zhenshan;Rong, Yiping;Li, Shijie;Zhang, Meifang;Yu, Lingjie;Feng, Teng;Zhang, Xiongwen;Wu, Xihan;Wu, Jim Z.;Chen, Li. And the article was included in Journal of Medicinal Chemistry in 2014.Electric Literature of C7H3ClIN The following contents are mentioned in the article:

Herein we report the identification of a novel class of HDAC6 and HDAC8 selective inhibitors through a unique chem. and phenotypic screening strategy. Tetrahydroisoquinoline 12 was identified as a potent HDAC6 and HDAC8 dual inhibitor from a focused library through cellular tubulin acetylation and p21 induction screening assays. Scaffold hopping from 12 led to the discovery of an aminotetralin class of HDAC inhibitors. In particular, the 3-R stereoisomer 32 showed highly potent inhibition against HDAC6 and HDAC8 with IC₅₀ values of 50 and 80 nM, resp. Treatment of neuroblastoma BE(2)C cells with 32 resulted in elevated levels of acetylated tubulin, TrkA, and neurite outgrowth with only marginal effects on p21 induction and histone H3 acetylation. Consistent with its weak enzymic inhibition of HDAC1, 32 showed significantly less cytotoxicity than SAHA and moderately inhibited the growth of myeloma NCI-H929 and OPM-2 cells. This study involved multiple reactions and reactants, such as 2-Chloro-4-iodobenzonitrile (cas: 371764-70-4Electric Literature of C7H3ClIN).

2-Chloro-4-iodobenzonitrile (cas: 371764-70-4) belongs to iodide derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Electric Literature of C7H3ClIN

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Intermediates in the synthesis of carboxyl-C¹⁴-labeled 3-hydroxyanthranilic acid was written by Ciereszko, Leon S.;Hankes, L. V.. And the article was included in Journal of the American Chemical Society in 1954.Recommanded Product: 725266-66-0 The following contents are mentioned in the article:

3,2-MeO(O₂N)C₆H₃CO₂H (I) (10 g.) and 15 g. SOCl₂ refluxed 1.5 h. on the water bath, the clear red solution dissolved in 50 cc. C₆H₆ and poured slowly and carefully with stirring into 200 cc. cold concentrated NH₄OH, the flask rinsed with 40 cc. Et₂O, the washings added to the NH₄OH solution, the mixture stirred 10 min., and the solid filtered off on a sintered glass funnel and washed successively with H₂O, EtOH, and Et₂O yielded 9.4 g. (94%) 3,2-MeO(O₂N)C₆H₃CONH₂ (II), colorless needles, m. 212°, very soluble in Me₂CO, but insoluble in H₂O, EtOH, Et₂O, and C₆H₆. It is recommended that the conversion of I to the acid chloride be carried out with SOCl₂ instead of PCl₅ which caused an explosion in one case. I (9.8 g.) in 200 cc. alk. 0.5N NaOCl stirred 3 h. at room temperature, the mixture filtered, the amber filtrate heated 0.5 h. at 80-90° and let stand overnight at room temperature, and the precipitate washed with H₂O and dried gave 7.5 g. (99%) 3,2-MeO(O₂N)C₆H₃NH₂ (III), bright yellow crystals, m. 124° (recrystallized from C₆H₆-ligroine, bright yellow needles, m. 124-4.5°). [The structure III had previously been assigned by Reverdin and Widmer (C.A. 8, 932) to a compound, m. 143°, obtained by the hydrolysis of 1 of the products isolated from a mixture produced by the nitration of m-MeOC₆H₄NHAc.] III (21 g.) in 300 cc. glacial AcOH treated gradually at 15° with 15 g. KNO₂ in 70 cc. ice-cold concentrated H₂SO₄, the resulting solution poured into 650 g. ice and H₂O, the mixture stirred 0.5 h., the excess HNO₂ destroyed with H₂NSO₃NH₄, the clear solution treated with 30 g. KI in 150 cc. H₂O, the mixture heated 1 h. on the water bath, and cooled, the liberated iodine removed with NaHSO₃, and the product filtered off, washed with H₂O, and dried gave 30.5 g. (88%) 3,2-MeO(O₂N)C₆H₃I (IV), reddish brown powder, m. 68-74°, which on short-path vacuum distillation gave pale yellow crystals, m. 81°. IV (2.7 g.) and 0.9 g. dry CuCN heated 2 h. at 180°, the mixture extracted with 25 cc. boiling C₆H₆, the extract diluted with 50 cc. ligroine, and the precipitate recrystallized from C₆H₆ and ligroine gave 3,2-MeO(O₂N)C₆H₃CN (V), white needles, m. 122°. IV (0.9 g.), 2.0 g. NaOH, 16 cc. H₂O, and 4 cc. EtOH refluxed 1.5 h. (evolution of NH₃), and the hot solution decolorized with C and acidified with HCl gave 1 g. I, m. 257°. This study involved multiple reactions and reactants, such as 1-Iodo-3-methoxy-2-nitrobenzene (cas: 725266-66-0Recommanded Product: 725266-66-0).

1-Iodo-3-methoxy-2-nitrobenzene (cas: 725266-66-0) belongs to iodide derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Recommanded Product: 725266-66-0

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of ring- and side-chain-substituted m-iodobenzylguanidine analogues was written by Vaidyanathan, Ganesan;Shankar, Sriram;Zalutsky, Michael R.. And the article was included in Bioconjugate Chemistry in 2001.Electric Literature of C7H8INO The following contents are mentioned in the article:

With the goal of developing m-iodobenzylguanidine (MIBG) analogs with improved targeting properties especially for oncol. applications, several radioiodinated ring- and side-chain-substituted MIBG analogs were synthesized. Except for 3-[¹³¹I]iodo-4-nitrobenzylguanidine (I) and N-hydroxy-3-[¹³¹I]iodobenzylguanidine (II), the radioiodinated analogs were prepared at no-carrier-added levels from their resp. tin precursors. The radiochem. yields generally were in the range of 70-90% except for 3-amino-5-[¹³¹I]iodobenzylguanidine for which a radiochem. yield of about 40% was obtained. While the silicon precursor N¹,N²-bis(tert-butyloxycarbonyl)-N¹-(4-nitro-3-trimethylsilylbenzyl)guanidine did not yield 3-[¹³¹I]iodo-4-nitrobenzylguanidine, its deprotected derivative, N¹-(4-nitro-3-trimethylsilylbenzyl)guanidine was radioiodinated in a modest yield of 20% providing 3-[¹³¹I]iodo-4-nitrobenzylguanidine. Exchange radioiodination of 3-iodo-4-nitrobenzylguanidine gave 3-[¹³¹I]iodo-4-nitrobenzylguanidine in 80% radiochem. yield. No-carrier-added [¹³¹I]NHIBG (III) was prepared from its silicon precursor N¹-hydroxy-N³-(3-trimethylsilylbenzyl)guanidine in 85% radiochem. yield. The paired-label tissue uptake of ¹²⁵I and ¹³¹I activity after injection of [¹²⁵I]MIBG, I, II, and III is provided. This study involved multiple reactions and reactants, such as (3-Amino-5-iodophenyl)methanol (cas: 368435-46-5Electric Literature of C7H8INO).

(3-Amino-5-iodophenyl)methanol (cas: 368435-46-5) belongs to iodide derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C7H8INO

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A convenient alumination of functionalized aromatics by using the frustrated Lewis pair Et₃Al and TMPMgCl-LiCl was written by Unsinn, Andreas;Wunderlich, Stefan H.;Jana, Anukul;Karaghiosoff, Konstantin;Knochel, Paul. And the article was included in Chemistry – A European Journal in 2013.Recommanded Product: 371764-70-4 The following contents are mentioned in the article:

A straightforward and efficient alumination of functionalized arenes, in particular, halogenated electron-rich aromatic compounds, with Et₃Al and stoichiometric amounts of frustrated Lewis pair TMPMgCl-LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) as a co-reactant, has been developed. In particular, halogenated electron-rich aromatics can be smoothly functionalized by using the frustrated Lewis pair Et₃Al and TMPMgCl-LiCl. Compared with previously described alumination methods, this procedure avoids extensive cooling and the need for an excess of base. This in situ procedure has proven to be most practical and allows for regio- and chemoselective metalation of a wide range of aromatics with sensitive functional groups (CONEt₂, CO₂Me, CN, OCONMe₂) or halogens (F, Cl, Br, I). The resulting aromatic aluminates, which were characterized by using NMR spectroscopy, were subjected to allylations, acylations, and palladium-catalyzed cross-coupling reactions after transmetalation to zinc. It was shown that the nature of the Zn salt used for transmetalation is crucial. Thus, compared with ZnCl₂ (2 equiv), the use of Zn(OPiv)₂ (2 equiv; OPiv=pivalate) allows the subsequent quenching reactions to be performed with only a slight excess of electrophile (1.2 equiv) and provides interesting functionalized aromatics in good yields. This study involved multiple reactions and reactants, such as 2-Chloro-4-iodobenzonitrile (cas: 371764-70-4Recommanded Product: 371764-70-4).

2-Chloro-4-iodobenzonitrile (cas: 371764-70-4) belongs to iodide derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Recommanded Product: 371764-70-4

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of diverse 3-Azido-5-(azidomethyl)benzene derivatives via formal C-H azidation and functional group-selective transformations was written by Nishiyama, Yoshitake;Misawa, Yoshihiro;Hazama, Yuki;Oya, Kazuhiro;Yoshida, Suguru;Hosoya, Takamitsu. And the article was included in Heterocycles in 2019.Quality Control of (3-Amino-5-iodophenyl)methanol The following contents are mentioned in the article:

3-Azido-5-(azidomethyl)benzene derivatives are useful compounds for preparing diverse bistriazole compounds and photoaffinity probes for target identification of bioactive compounds To more easily synthesize a diverse range of diazido compounds, a facile method for synthesizing diazido compounds bearing a transformable functional group, such as iodo, bromo, methoxycarbonyl, or cyano group, was developed. This method is based on formal C-H azidation of 1,3-disubstituted benzenes via regioselective borylation followed by deborylative azidation with subsequent transformations, such as that of a one-carbon unit on the benzene ring to an azidomethyl group. The functional groups of the diazido compounds were efficiently transformed to various connecting groups, including carboxy, (succinimidyloxy)carbonyl, hydroxymethyl, formyl, bromomethyl, tosylthiomethyl, ethynyl, diazoacetyl, bromoacetyl, boryl, hydroxy, aminocarbonyl, amino, and isothiocyanato groups, leaving the azido groups untouched. Several diazido building blocks were used to prepare diazido compounds by forming amide, thiourea, and sulfide bonds via conjugation at the connecting groups. These results show that the method described here would facilitate diazido probe syntheses and bistriazole library construction. This study involved multiple reactions and reactants, such as (3-Amino-5-iodophenyl)methanol (cas: 368435-46-5Quality Control of (3-Amino-5-iodophenyl)methanol).

(3-Amino-5-iodophenyl)methanol (cas: 368435-46-5) belongs to iodide derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of (3-Amino-5-iodophenyl)methanol

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Discovery and biological evaluation of novel androgen receptor antagonist for castration-resistant prostate cancer was written by Yu, Jiang;Zhang, Lanxi;Yan, Guoyi;Zhou, Peiting;Cao, Chaoguo;Zhou, Fei;Li, Xinghai;Chen, Yuanwei. And the article was included in European Journal of Medicinal Chemistry in 2019.Quality Control of 2-Chloro-4-iodobenzonitrile The following contents are mentioned in the article:

Prostate cancer (PC) is the second most common malignancy in men worldwide. Among current therapies, two antiandrogens, Abiraterone Acetate and Enzalutamide (Enza) have become the standard of care for patients with metastatic castration-resistant prostate cancer (mCRPC). Here, the authors designed and synthesized a new series of nonsteroidal compounds deriving from the hybridization of Abiraterone (Abi) and Enzalutamide, among which compound I featuring the diphenylamine scaffold was identified as a potent and cell selective androgen receptor (AR) antagonist. In cell proliferation assays, compound I exhibited better antiproliferative activities than Enzalutamide against AR-overexpressing VCaP cells and 22Rv1 cells bearing H874Y-mutated AR. In addition, I suppressed the activity of AR-F876L mutant that confers resistance to Enzalutamide and efficiently blocked R1881-induced PSA and FKBP5 gene expression. In competitive binding assay, compound I displayed higher binding affinity to AR than Enzalutamide. These results suggest compound I as a potential candidate to treat Enza-resistant CRPC. This study involved multiple reactions and reactants, such as 2-Chloro-4-iodobenzonitrile (cas: 371764-70-4Quality Control of 2-Chloro-4-iodobenzonitrile).

2-Chloro-4-iodobenzonitrile (cas: 371764-70-4) belongs to iodide derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of 2-Chloro-4-iodobenzonitrile

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com