Tag: 200-300

Defining the Mechanism of Action and Enzymatic Selectivity of Psammaplin A against Its Epigenetic Targets was written by Baud, Matthias G. J.;Leiser, Thomas;Haus, Patricia;Samlal, Sharon;Wong, Ai Ching;Wood, Robert J.;Petrucci, Vanessa;Gunaratnam, Mekala;Hughes, Siobhan M.;Buluwela, Lakjaya;Turlais, Fabrice;Neidle, Stephen;Meyer-Almes, Franz-Josef;White, Andrew J. P.;Fuchter, Matthew J.. And the article was included in Journal of Medicinal Chemistry in 2012.COA of Formula: C8H7IO2 This article mentions the following:

Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the mol. features of this mol. responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC₅₀ 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotoxicity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6COA of Formula: C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.COA of Formula: C8H7IO2

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

Mild and efficient iodination of aromatic compounds with pyridine-iodine monochloride complex (PylCl) was written by Muathen, Hussni A.. And the article was included in Journal of Chemical Research, Synopses in 1994.Product Details of 20776-54-9 This article mentions the following:

A wide range of aromatic compounds (e.g., C₆H₆) have been effectively iodinated with a pyridine-iodine monochloride complex (I). Condensed polycyclic iodides, which are not readily obtained via direct iodination, can be prepared indirectly via their corresponding organomercurials in 1 step. Some benzoid and nonbenzoid heterocycles (e.g., indole) are iodinated with I. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Product Details of 20776-54-9).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Product Details of 20776-54-9

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

Application of Oppolzer’s sultam in the synthesis of cyclic α-amino acids and β-amino acids was written by Wozniak, D.;Szymanska, A.;Oldziej, S.;Lankiewicz, L.;Grzonka, Z.. And the article was included in Polish Journal of Chemistry in 2006.Product Details of 10297-05-9 This article mentions the following:

In this paper we describe the application of Oppolzer’s sultam as a chiral auxiliary for the synthesis of cyclic α- and β²-amino acids. The key step of the synthesis is stereoselective alkylation of sultam-derived glycine and β-alanine Schiff’s bases leading to diastereometrically pure products. Final compounds are obtained after mild acidic and then basic hydrolyzes of auxiliary groups and can be directly converted into N-tert-butoxycarbonyl- or N-fluorenylmethoxycarbonyl derivatives useful in peptide synthesis. In the case of substrates alkylated with dihaloalkanes spontaneous cyclization occurring during removal of the auxiliary groups yields cyclic α-amino acids (proline homologues) with reasonable yield and stereoselectivity. Theor. data explain the differences in tendency for cyclization between α- and β-amino acids. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Product Details of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Product Details of 10297-05-9

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

Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides was written by Yang, Chao;Pohl, Radek;Tichy, Michal;Gurska, Sona;Pavlis, Petr;Dzubak, Petr;Hajduch, Marian;Hocek, Michal. And the article was included in Journal of Organic Chemistry in 2020.Product Details of 36748-88-6 This article mentions the following:

Two isomeric series of benzothieno-fused 7-deazapurine (benzo[4′,5′]thieno[3′,2′:4,5]- and benzo[4′,5′]thieno[2′,3′:4,5]pyrrolo[2,3-d]pyrimidine) ribonucleosides were designed and synthesized. Key steps of the synthesis included the Negishi coupling of zincated dichloropyrimidine with 2- or 3-iodobenzothiophene followed by azidation, thermal or photochem. cyclization, glycosylation, and final functionalization at position 6 through cross-couplings or nucleophilic substitutions. Deprotection gave the final nucleosides, some of which showed moderate cytotoxic and antiviral activity. Most of the free nucleosides showed moderate to strong fluorescence with emission maxima of 362-554 nm. 2′-Deoxyribonucleoside and its 5′-O-triphosphate were also prepared from benzothieno-fused 7-deazaadenine derivative, and the triphosphate was a good substrate for KOD XL DNA polymerase in primer extension synthesis of modified DNA which exerted a weak fluorescence which was slightly enhanced in double-stranded DNA as compared to single-stranded oligonucleotides. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Product Details of 36748-88-6).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Product Details of 36748-88-6

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

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 was written by Fu, Zhengjiang;Jiang, Ligao;Zuo, Qianming;Li, Zhaojie;Liu, Yanzhu;Wei, Zhenhong;Cai, Hu. And the article was included in Organic & Biomolecular Chemistry in 2018.Application In Synthesis of 4-Chloro-2-iodo-1-nitrobenzene This article mentions the following:

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. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Application In Synthesis of 4-Chloro-2-iodo-1-nitrobenzene).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Application In Synthesis of 4-Chloro-2-iodo-1-nitrobenzene

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

Rapid Access to Aliphatic Sulfonamides was written by Zhang, Mingjun;Yu, Mo;Wang, Ziwen;Liu, Yuxiu;Wang, Qingmin. And the article was included in Organic Letters in 2022.Computed Properties of C4H8ClI This article mentions the following:

Herein, a mild, rapid, straightforward method for visible-light-mediated sulfonamide ethylation to afford a diverse array of compounds with C(sp³)-sulfonamide skeletons RS(O)₂N(R¹)R² (R = 4-phenylbutyl, 3,3-dimethylbutyl, 2-cyclobutylethyl, 4-(pyridin-2-yl)butyl, etc.; R¹ = H, Ph, 2-oxooxolan-3-yl, benzyl, etc.; R² = H, Me, phenyl) was reported. The method relies on inexpensive, abundant, com. available primary, secondary, and tertiary alkyl carboxylic acids I (R³ = 2-phenylethyl, 2,2-diphenylethyl, 2-(pyridin-3-yl)ethyl, pentyl, etc.) and alkyl iodides R⁴I (R⁴ = 2-cyclohexylethyl, pentyl, 4-(trimethylsilyl)butyl, hept-6-yn-1-yl, etc.) as substrates. The method has a broad substrate scope and potential utility for late-stage functionalization of natural products and synthetic medicines and can be expected to facilitate rapid structural diversification of bioactive mols. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Computed Properties of C4H8ClI).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Computed Properties of C4H8ClI

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

Enhancing Repair of Oxidative DNA Damage with Small-Molecule Activators of MTH1 was written by Lee, Yujeong;Onishi, Yoshiyuki;McPherson, Lisa;Kietrys, Anna M.;Hebenbrock, Marian;Jun, Yong Woong;Das, Ishani;Adimoolam, Shanthi;Ji, Debin;Mohsen, Michael G.;Ford, James M.;Kool, Eric T.. And the article was included in ACS Chemical Biology in 2022.Category: iodides-buliding-blocks This article mentions the following:

Here, it is reported that selected tyrosine kinase (TK) inhibitors including nilotinib, employed clin. in the treatment of chronic myeloid leukemia, are activators of the repair enzyme Human MutT Homolog 1 (MTH1). MTH1 cleanses the oxidatively damaged cellular nucleotide pool by hydrolyzing the oxidized nucleotide 8-oxo-2′-deoxyguanosine (8-oxo-dG)TP, which is a highly mutagenic lesion when incorporated into DNA. Structural optimization of analogs of TK inhibitors resulted in compounds such as SU0448, which induces 1000 +/- 100% activation of MTH1 at 10μM and 410 +/- 60% at 5μM. The compounds are found to increase the activity of the endogenous enzyme, and at least one (SU0448) decreases levels of 8-oxo-dG in cellular DNA. The results suggest the possibility of using MTH1 activators to decrease the frequency of mutagenic nucleotides entering DNA, which may be a promising strategy to suppress tumorigenesis in individuals with elevated cancer risks. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Category: iodides-buliding-blocks).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Category: iodides-buliding-blocks

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

Highly Z-selective synthesis of 1,3-oxathiol-2-ylidenes and 4-methylene-oxazolidine-2-thiones via atom-specific 5-exo-dig cyclization of propargyl alcohol with isothiocyanate was written by Antony Savarimuthu, S.;Leo Prakash, D. G.;Augustine Thomas, S.;Gandhi, Thirumanavelan;Bera, Mrinal K.. And the article was included in Organic & Biomolecular Chemistry in 2020.Application In Synthesis of 1,2-Difluoro-3-iodobenzene This article mentions the following:

A series of 3,4,5-trisubstituted (Z)-1,3-oxathiol-2-ylidenes I (R = 2-ClC₆H₄, 4-t-BuC₆H₄, etc.; R¹ = Ph, 2-FC₆H₄, 4-BrC₆H₄, etc.; R² = Ph, 4-FC₆H₄) was synthesized via DBU-mediated 5-exo-dig cyclization of isothiocyanates RNCS and propargyl alcs. R¹CH(OH)CCR². Exclusive S-nucleophilic cyclization was observed with propargyl alcs. R³CCCH₂OH (R³ = Ph, 2,3-F₂C₆H₃, 4-O₂NC₆H₄, etc.) and isothiocyanates RNCS to produce the corresponding 3,4-disubstituted (Z)-N-(Z)-4-ethylidene-1,3-oxathiolan-2-ylidenes II. Also, the parent propargyl alc. and isothiocyanates underwent an N-nucleophilic attack to afford 4-methyleneoxazolidine-2-thiones III. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Application In Synthesis of 1,2-Difluoro-3-iodobenzene).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Application In Synthesis of 1,2-Difluoro-3-iodobenzene

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

Fine electronic state tuning of cobaltadithiolene complexes by substituent groups on the benzene ring was written by Tsukada, Satoru;Kondo, Masataka;Sato, Hironobu;Gunji, Takahiro. And the article was included in Polyhedron in 2016.Electric Literature of C6H3F2I This article mentions the following:

A series of 3,6- and 4,5-dihalogen-substituted 1,2-benzenedithiol (H₂bdt) ligands, (3,6-X¹₂-4,5-X²₂-1,2-H₂bdt) (X² = H, X¹ = F (1a), Cl (1b), Br (1c); X¹ = H, X² = Cl (4)), and their cobalt complexes, [Cp^*Co(3,6-X¹₂-4,5-X²₂-1,2-bdt)] (X² = H, X¹ = F (2a), Cl (2b), Br (2c); X¹ = H, X² = Cl (5)), were synthesized by a modified selective thiolation reaction. The 1,2-diphenyl-substituted cobaltadithiolene complex (2d) was also synthesized. The mol. structures of all cobaltadithiolene complexes were determined by single crystal X-ray diffraction anal. Compounds 2a, 5 and 12 showed unique packing structures with intermol. interactions that confirmed them as the first examples of half-sandwich-type metalladithiolene complexes with a Cp^* ligand. The effects of the benzene substituent type and position on the metalladithiolene ring were investigated using UV-vis spectroscopy measurements and cyclic voltammetry. The results indicate that substitution of halogen atoms at the 3 and 6 position of the benzene ring had a larger effect on the dithiolene ring than substitution at the 4 and 5 positions. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Electric Literature of C6H3F2I).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Electric Literature of C6H3F2I

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

Studies on spiro[4.5]decanone prolyl hydroxylase domain inhibitors was written by Holt-Martyn, James P.;Tumber, Anthony;Rahman, Mohammed Z.;Lippl, Kerstin;Figg, William Jr;McDonough, Michael A.;Chowdhury, Rasheduzzaman;Schofield, Christopher J.. And the article was included in MedChemComm in 2019.COA of Formula: C6H4INO2 This article mentions the following:

The 2-oxoglutarate (2OG) dependent hypoxia inducible factor (HIF) prolyl hydroxylases (PHDs) are targets for treatment of anemia and other ischemia related diseases. PHD inhibitors are in clin. trials; however, the number of reported templates for PHD inhibition is limited. We report structure-activity relationship and crystallog. studies on spiro[4.5]decanone containing PHD inhibitors. Together with other studies, our results reveal spiro[4.5]decanones as useful templates for generation of potent and selective 2OG oxygenase inhibitors. In the experiment, the researchers used many compounds, for example, 2-Iodopyridine-4-carboxylic acid (cas: 58481-10-0COA of Formula: C6H4INO2).

2-Iodopyridine-4-carboxylic acid (cas: 58481-10-0) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.COA of Formula: C6H4INO2

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