Category: iodides-buliding-blocks

Hinge Binder Scaffold Hopping Identifies Potent Calcium/Calmodulin-Dependent Protein Kinase Kinase 2 (CAMKK2) Inhibitor Chemotypes was written by Eduful, Benjamin J.;O’Byrne, Sean N.;Temme, Louisa;Asquith, Christopher R. M.;Liang, Yi;Picado, Alfredo;Pilotte, Joseph R.;Hossain, Mohammad Anwar;Wells, Carrow I.;Zuercher, William J.;Catta-Preta, Carolina M. C.;Zonzini Ramos, Priscila;Santiago, Andre de S.;Counago, Rafael M.;Langendorf, Christopher G.;Nay, Kevin;Oakhill, Jonathan S.;Pulliam, Thomas L.;Lin, Chenchu;Awad, Dominik;Willson, Timothy M.;Frigo, Daniel E.;Scott, John W.;Drewry, David H.. And the article was included in Journal of Medicinal Chemistry in 2021.Safety of 5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine This article mentions the following:

CAMKK2 is a serine/threonine kinase and an activator of AMPK whose dysregulation is linked with multiple diseases. Unfortunately, STO-609, the tool inhibitor commonly used to probe CAMKK2 signaling, has limitations. To identify promising scaffolds as starting points for the development of high-quality CAMKK2 chem. probes, we utilized a hinge-binding scaffold hopping strategy to design new CAMKK2 inhibitors. Starting from the potent but promiscuous disubstituted 7-azaindole GSK650934, a total of 32 compounds, composed of single-ring, 5,6-, and 6,6-fused heteroaromatic cores, were synthesized. The compound set was specifically designed to probe interactions with the kinase hinge-binding residues. Compared to GSK650394 and STO-609, 13 compounds displayed similar or better CAMKK2 inhibitory potency in vitro, while compounds 13g and 45 had improved selectivity for CAMKK2 across the kinome. Our systematic survey of hinge-binding chemotypes identified several potent and selective inhibitors of CAMKK2 to serve as starting points for medicinal chem. programs. In the experiment, the researchers used many compounds, for example, 5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine (cas: 923595-58-8Safety of 5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine).

5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine (cas: 923595-58-8) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Safety of 5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine

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

Design, synthesis and structure-activity relationship optimization of phenanthridine derivatives as new anti-vitiligo compounds was written by Yang, Bi-juan;Fan, Shi-rui;Zhang, Xin-fang;Cai, Jie-yun;Ruan, Ting;Xiang, Zheng-rui;Ren, Juan;Hao, Xiao-jiang;Chen, Duo-zhi. And the article was included in Bioorganic Chemistry in 2022.Electric Literature of C4H5IN2 This article mentions the following:

Humans have been suffering from vitiligo for a long time. Target vitiligo drugs have yet been approved. Activation of Wnt/β-catenin signalling has potential in the therapeutic use of vitiligo, so exploring new drugs that specifically directly activate Wnt is worthwhile to obtain new anti-vitiligo agents. In this work, two portions design and synthesis were put into effect. firstly, 17 phenanthridine derivatives with C-4 substitutes were designed and synthesized, which compounds 4, 6, 12, 13 served as H-acceptor with protein showed enhance melanogenesis activity; Secondly, 7 hybrid new scaffolds of compounds were designed and synthesized, scaffold hopping compound 36 that aromatic benzene was replaced pyrazole on ring C showed enhance melanogenesis and tyrosinase activity; The last and most important, a comprehensive optimization and SARs of compound 36 were carried out, compounds 41 and 43 shared phenolic hydroxyl or 3-methyl-pyridine substitutes at C-7 position remarkably improved the capacity of melanogenesis and tyrosinase activity. Compound 43 were identified as new anti-vitiligo agents that specifically activate the Wnt/β-catenin signalling pathway by targeting Axin. Structure-activity relationship anal. implied that H-acceptor substitutions at the C-4 position and phenolic hydroxyl or pyridine substitutions at the C-7 position would improve the activities of the compounds These findings reveal a new therapeutic strategy for vitiligo, and compounds 41 and 43 may represent potential compounds for vitiligo treatment. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Electric Literature of C4H5IN2).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. 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.Electric Literature of C4H5IN2

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

From supramolecular porphyrin tweezers to dynamic A_nB_mC_lD_k multiporphyrin arrangements through orthogonal coordination was written by Kishore, Ravuri S. K.;Paululat, Thomas;Schmittel, Michael. And the article was included in Chemistry – A European Journal in 2006.Product Details of 3268-21-1 This article mentions the following:

A dynamic, supramol., three-component A_nB_mC₁ bis(zinc porphyrin) tweezer,containing Cu(I), I (R = 2,4,6-trimethylphenyl, R¹ = 4-bromo-2,3,5,6-tetramethylphenyl), and II (R² = dodecyl) was prepared quant. using the heteroleptic bisphenanthroline (HETPHEN) concept. Upon addition of nitrogenous spacers of different length, namely, the extended 1,4-bis(4′-pyridylethynyl)durene (3a), 4,4′-bipyridine (3b), and 1,4-diazabicyclo[2.2.2]octane (DABCO; 3c), to set up an addnl. orthogonal binding motif (Zn_Por-N_spacer), three structurally different, still dynamic, four-component A_nB_mC₁D_k assemblies were cleanly formed, as indicated by UV/visible and NMR titrations as well as by DOSY studies. The structures were identified as a bridged monotweezer A₂BC₂D, a doubly bridged double tweezer A₄B₂C₄D₂, and a triply bridged double tweezer A₄B₂C₄D₃, the latter resembling a porphyrin stack. Notably, the same structures were equally formed directly from a mixture of the constituents A, B, C, and D put together in any sequence if the correct stoichiometry was applied. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Product Details of 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) 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. 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.Product Details of 3268-21-1

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

2,4-Disubstituted thiazoles by regioselective cross-coupling or bromine-magnesium exchange reactions of 2,4-dibromothiazole was written by Gross, Stefan;Heuser, Stefan;Ammer, Carolin;Heckmann, Golo;Bach, Thorsten. And the article was included in Synthesis in 2011.Recommanded Product: 10297-05-9 This article mentions the following:

Cross-coupling reactions occur on 2,4-dibromothiazole preferentially at the more electron-deficient 2-position. This fact can be favorably used to prepare 2-substituted 4-bromothiazoles, e.g. I, which serve as precursors for 2,4-disubstituted thiazoles, e.g. II. Protocols for regioselective Negishi and Stille cross-coupling reactions are provided. Alternatively, the title compound can be metalated in 2-position by a halogen-metal exchange reaction. As a supplement to the well-established bromine-lithium exchange, the regioselective bromine-magnesium exchange reaction is presented. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Recommanded Product: 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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. 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.Recommanded Product: 10297-05-9

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

Synthesis of carboxylic acid N-hydroxynorborn-5-ene-2,3-dicarboximide esters was written by Henklein, Peter;Ott, Tilmann;Jaehrling, Renate;Scharfenberg, Peter;Heyne, Hans Ulrich;Niedrich, Hartmut. And the article was included in Zeitschrift fuer Chemie in 1989.Electric Literature of C6H4INO2 This article mentions the following:

A one pot preparation of title compounds R¹CO₂R (R¹ = e.g., Ph, naphthyl, adamantyl) is described. Thus condensation reaction of ClCO₂R with arylcarboxylic or amino acids, R¹CO₂H, in CH₂Cl₂, THF, or THF-dioxane (1:1) in the presence of N-methylmorpholine using 4-(dimethylamino)pyridine as catalyst gave R¹CO₂CO₂R, which is unstable and loses CO₂ to give 64-87% R¹CO₂R. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Electric Literature of C6H4INO2).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Electric Literature of C6H4INO2

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

Nickel-catalyzed direct formation of the C-S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent was written by Wang, Yang;Zhang, Xiaofeng;Liu, Haixiong;Chen, Hui;Huang, Deguang. And the article was included in Organic Chemistry Frontiers in 2017.SDS of cas: 5460-32-2 This article mentions the following:

Various unsym. aryl sulfides were synthesized by nickel-catalyzed C-S bond formation in good to excellent yields. The reactions employed arylsulfonyl chlorides as an aryl thiol source and Mn dust as a reducing agent. The scope and versatility of the method was successfully demonstrated with 42 examples. Mechanistic studies revealed the existence of an intermediate disulfide substance. A catalytic cycle was proposed including a three-step reduction by Mn for the achievement of the reaction, and Ni(0) and Ni(I) species were supposed to be involved in the reaction mechanism. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2SDS of cas: 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.SDS of cas: 5460-32-2

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

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors was written by Rohrig, Ute F.;Majjigapu, Somi Reddy;Reynaud, Aline;Pojer, Florence;Dilek, Nahzli;Reichenbach, Patrick;Ascencao, Kelly;Irving, Melita;Coukos, George;Vogel, Pierre;Michielin, Olivier;Zoete, Vincent. And the article was included in Journal of Medicinal Chemistry in 2021.Quality Control of 4-Chloro-2-iodo-1-nitrobenzene This article mentions the following:

The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism Many IDO1 inhibitors with different chemotypes have been developed, mainly targeted for use in anti-cancer immunotherapy. Lead optimization of direct heme iron-binding inhibitors has proven difficult due to the remarkable selectivity and sensitivity of the heme-ligand interactions. Here, we present exptl. data for a set of closely related small azole compounds with more than 4 orders of magnitude differences in their inhibitory activities, ranging from millimolar to nanomolar levels. We investigate and rationalize their activities based on structural data, mol. dynamics simulations, and d. functional theory calculations Our results not only expand the presently known four confirmed chemotypes of sub-micromolar heme binding IDO1 inhibitors by two addnl. scaffolds but also provide a model to predict the activities of novel scaffolds. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Quality Control of 4-Chloro-2-iodo-1-nitrobenzene).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Quality Control of 4-Chloro-2-iodo-1-nitrobenzene

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

Structure-antitumor activity relationship of hybrid acetogenins focusing on connecting groups between heterocycles and the linker moiety was written by Ohta, Kaito;Fushimi, Tetsuya;Okamura, Mutsumi;Akatsuka, Akinobu;Dan, Shingo;Iwasaki, Hiroki;Yamashita, Masayuki;Kojima, Naoto. And the article was included in RSC Advances in 2022.Quality Control of 5-Iodo-1-methyl-1H-pyrazole This article mentions the following:

We studied hybrid mols. of annonaceous acetogenins and mitochondrial complex I-inhibiting insecticides to develop a novel anticancer agent. A structure-antitumor activity relationship study focusing on the connecting groups between the heterocycles and the linker moiety bearing the THF moiety was conducted. Eleven hybrid acetogenins with 1-methylpyrazole instead of γ-lactone were synthesized and their growth inhibitory activities against 39 human cancer cell lines were evaluated. The nitrogen atom at the 2′-position of the linker moiety was essential for inhibiting cancer growth. The 1-methylpyrazole-5-sulfonamide analog showed potent growth inhibition of NCI-H23, a human lung cancer cell line, in a xenograft mouse assay without critical toxicity. Hence, the results of this study may pave the way for the development of novel anticancer agents, with both selective and broad anticancer activities. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Quality Control of 5-Iodo-1-methyl-1H-pyrazole).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) 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. 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.Quality Control of 5-Iodo-1-methyl-1H-pyrazole

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

TMSCF₃ as a Convenient Source of CF₂=CF₂ for Pentafluoroethylation, (Aryloxy)tetrafluoroethylation, and Tetrafluoroethylation was written by Li, Lingchun;Ni, Chuanfa;Xie, Qiqiang;Hu, Mingyou;Wang, Fei;Hu, Jinbo. And the article was included in Angewandte Chemie, International Edition in 2017.Application In Synthesis of 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

A new method for the on-site preparation of tetrafluoroethylene (TFE) and a procedure for its efficient use in fluoroethylation reactions were developed using a simple two-chamber system. The on-site preparation of TFE was accomplished by dimerization of difluorocarbene derived from (trifluoromethyl)trimethylsilane (TMSCF₃) under mild conditions. TFE was further used for pentafluoroethylation of various aryl iodides alkylation reactions, such as (aryloxy)tetrafluoroethylation of aryl and heteroaryl iodides and tetrafluoroethylation of heteroatom nucleophiles, such as phenols, alcs., thiols and amines. This work not only demonstrates a convenient and safe approach for the generation and use of TFE in academic laboratories, but also provides a new strategy for pentafluoroethylation. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Application In Synthesis of 4-Iodo-1,2-dimethoxybenzene).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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-Iodo-1,2-dimethoxybenzene

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