February 2023 - Page 113 of 117 - Indole Building Blocks

Trinh, Trieu N. et al. published their research in Organic & Biomolecular Chemistry in 2016 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 5-Chloroindole-3-carboxaldehyde

Quinolone-1-(2H)-ones as hedgehog signalling pathway inhibitors was written by Trinh, Trieu N.;McLaughlin, Eileen A.;Abdel-Hamid, Mohammed K.;Gordon, Christopher P.;Bernstein, Ilana R.;Pye, Victoria;Cossar, Peter;Sakoff, Jennette A.;McCluskey, Adam. And the article was included in Organic & Biomolecular Chemistry in 2016.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of quinolone-2-(1H)-ones derived from the Ugi-Knoevenagel three- and four-component reaction were prepared exhibiting low micromolar cytotoxicity against a panel of eight human cancer cell lines known to possess the hedgehog signalling pathway (HSP) components, as well as the seminoma TCAM-2 cell line. A focused SAR study was conducted and revealed core characteristics of the quinolone-2-(1H)-ones required for cytotoxicity. These requirements included a C3-tethered indole moiety, an indole C5-Me moiety, an aliphatic tail or an ester, as well as an addnl. aromatic moiety. Further investigation in the SAG-activated Shh-LIGHT2 cell line with the most active analogs such as 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(1-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide, 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(5-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide and Et (2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(5-methyl-1H-indol-3-yl)acetyl)glycinate demonstrated a down regulation of the HSP via a reduction in Gli expression and in the mRNA levels of Ptch₁ and Gli₂ and these compounds returned in cell inhibition values of 11.6, 2.9 and 3.1 μM, resp. making this new HSP-inhibitor pharmacophore amongst the most potent non-Smo inhibitors thus far reported. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Kosuge, Yasuhiro et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C11H11NO2

Indirubin derivatives protect against endoplasmic reticulum stress-induced cytotoxicity and down-regulate CHOP levels in HT22 cells was written by Kosuge, Yasuhiro;Saito, Hiroaki;Haraguchi, Tatsuki;Ichimaru, Yoshimi;Ohashi, Sachiyo;Miyagishi, Hiroko;Kobayashi, Shunsuke;Ishige, Kumiko;Miyairi, Shinichi;Ito, Yoshihisa. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Formula: C11H11NO2 This article mentions the following:

Indirubin and its derivatives have been reported to exhibit anticancer and anti-inflammatory activities. Recently, some of its derived analogs have been shown to have neuroprotective potential. Endoplasmic reticulum (ER) stress has been demonstrated to contribute to the pathogenesis of various neurodegenerative diseases, whereas the effects of indirubin derivatives on ER stress-induced cell death have not been addressed. In the present study, a series of 44 derivatives of indirubin was prepared to search for a novel class of neuroprotective agents against ER stress-induced neuronal death. The MTT reduction assay indicated that tunicamycin (TM), an inducer of ER stress, significantly decreased the viability of hippocampal neuronal HT22 cells. Among the compounds tested, eight showed significant inhibitory activity against TM-induced cell death. Western blot anal. showed that application of these analogs to the cells simultaneously with TM reduced the TM-induced expression of CHOP, an established mediator of ER stress. The results suggest that the preventive effect of these indirubin derivatives against ER stress-induced neuronal death may be due, at least in part, to attenuation of the CHOP-dependent signaling system. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Formula: C11H11NO2).

Wang, Dawei et al. published their research in Synlett in 2016 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Safety of 4-Bromo-1H-indole-2-carboxylic acid

Transition-Metal-Free Direct Arylation and Esterification Reaction of Unprotected Indolylcarboxylic Acid Derivatives: A New Entry to 2-(1H-Indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and Aryl 1H-Indole-2-carboxylates was written by Wang, Dawei;Ge, Chenyang;Yu, Xin;Wan, Huida;Xu, Xiang. And the article was included in Synlett in 2016.Safety of 4-Bromo-1H-indole-2-carboxylic acid This article mentions the following:

An efficient, ligand-free, transition-metal-free, direct arylation and esterification reaction of unprotected indolylcarboxylic acid derivatives with diaryliodonium salts was developed, thus providing a new entry to 2-(1H-indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and aryl 1H-indole-2-carboxylate derivatives I (R = H, 4-MeO, 4-F, 5-NO₂, 4-Br; Ar = Ph, 4-MeC₆H₄) with good yields. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Safety of 4-Bromo-1H-indole-2-carboxylic acid).

Kuett, Agnes et al. published their research in European Journal of Organic Chemistry in 2021 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole 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.Reference of 4769-96-4

Strengths of Acids in Acetonitrile was written by Kuett, Agnes;Tshepelevitsh, Sofja;Saame, Jaan;Lokov, Maert;Kaljurand, Ivari;Selberg, Sigrid;Leito, Ivo. And the article was included in European Journal of Organic Chemistry in 2021.Reference of 4769-96-4 This article mentions the following:

The equilibrium acidity scale (pK_a scale) in acetonitrile has been supplemented by numerous new compounds and new ΔpK_a measurements. It now contains altogether 231 acids – over twice more than published previously – linked by 569 ΔpK_a measurements and spans between the pK_a values of hydrogen iodide (2.8) and indole (32.57), covering close to 30 orders of magnitude. Measurement results acquired over the last 15 years were added to the scale and new least-squares treatment was carried out. The treatment yielded revised pK_a values for the compounds published previously, with the root mean square difference between revised and previous values 0.04, demonstrating very good stability of the scale. Correlation equations were developed for estimating pK_a values for the studied types of compounds in water, DMSO, DMF, and 1,2-dichloroethane on the basis of pK_a values in acetonitrile. These equations enable predicting pK_a values with an average error around or less than 1 pK_a unit, which is a sufficient accuracy for many applications. The scale is expected to be a useful tool for the widest possible research areas in organic chem., electrochem. power sources, catalysis, etc. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 4769-96-4).

Mei, Haibo et al. published their research in Organic Letters in 2022 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Quality Control of 5-Chloroindole-3-carboxaldehyde

Visible-Light-Irradiated Cascade Reaction of Indole-Tethered Alkenes to Access Tetracyclic Tetrahydro-γ-carbolines was written by Mei, Haibo;Liu, Aiyao;He, Jingrui;Yu, Yingjie;Han, Jianlin. And the article was included in Organic Letters in 2022.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of indole-derived alkenes I (R = H, Cl, Br; R¹ = Me, OMe, F, etc.; R² = H, Me, F, etc.; R³ = R⁴ = H, Me; Ar = Ph, 4-methylphenyl, 4-bromophenyl, 4-methyoxphenyl) have been designed and applied in a photocatalytic cascade reaction with bromodifluoroacetate esters BrCF₂C(O)OR⁵ (R⁵ = Me, Bn, cyclopentyl, etc.), affording an unknown type of tetracyclic tetrahydro-γ-carboline derivative II in up to 90% yields. Mechanistic studies suggest that the reaction proceeds with tetrahydro-γ-carboline III (Ar = 4-methylphenyl, R⁵ = Et;) as a key intermediate. The reaction tolerates a diverse pool of substrates, which provides an efficient method for the construction of tetracyclic tetrahydro-γ-carboline II compounds In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Rogness, Donald C. et al. published their research in Tetrahedron Letters in 2009 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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 Methyl 5-fluoro-1H-indole-2-carboxylate

Rapid synthesis of the indole-indolone scaffold via [3+2] annulation of arynes by methyl indole-2-carboxylates was written by Rogness, Donald C.;Larock, Richard C.. And the article was included in Tetrahedron Letters in 2009.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

The reaction of Me indole-2-carboxylates, e.g., I, and arynes afforded a very efficient, high yielding synthesis of a novel indole-indolone ring system, e.g., II, which tolerated considerable functionality, was broad in scope, and proceeded under mild reaction conditions. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate).

Klose, Jana et al. published their research in Tetrahedron in 1997 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C14H9NO2S

Preparation of 2-[(2-cyanoethyl)thio]-1H-isoindole-1,3(2H)-dione and related sulfur-transfer agents was written by Klose, Jana;Reese, Colin B.;Song, Quanial. And the article was included in Tetrahedron in 1997.Formula: C14H9NO2S This article mentions the following:

The title compound (I, R = CH₂CH₂CN) and a morpholine analog (II) are both conveniently prepared in good yield from 2-cyanoethyl disulfide, which itself is readily prepared in one step from S-(2-cyanoethyl)isothiouronium chloride. In the same way, di-Me and di-Ph disulfides are converted to I (R = Me, Ph, resp.), also in good yields. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Goodfellow, Val S. et al. published their research in Journal of Medicinal Chemistry in 2013 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole 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. 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: 7-Azaindole-5-boronic Acid Pinacol Ester

Discovery, Synthesis, and Characterization of an Orally Bioavailable, Brain Penetrant Inhibitor of Mixed Lineage Kinase 3 was written by Goodfellow, Val S.;Loweth, Colin J.;Ravula, Satheesh B.;Wiemann, Torsten;Nguyen, Thong;Xu, Yang;Todd, Daniel E.;Sheppard, David;Pollack, Scott;Polesskaya, Oksana;Marker, Daniel F.;Dewhurst, Stephen;Gelbard, Harris A.. And the article was included in Journal of Medicinal Chemistry in 2013.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Inhibition of mixed lineage kinase 3 (MLK3) is a potential strategy for treatment of Parkinson’s disease and HIV-1 associated neurocognitive disorders (HAND), requiring an inhibitor that can achieve significant brain concentration levels. We report here URMC-099 (1) an orally bioavailable (F = 41%), potent (IC₅₀ = 14 nM) MLK3 inhibitor with excellent brain exposure in mouse PK models and minimal interference with key human CYP450 enzymes or hERG channels. The compound inhibits LPS-induced TNFα release in microglial cells, HIV-1 Tat-induced release of cytokines in human monocytes and up-regulation of phospho-JNK in Tat-injected brains of mice. Compound 1 likely functions in HAND preclin. models by inhibiting multiple kinase pathways, including MLK3 and LRRK2 (IC₅₀ = 11 nM). We compare the kinase specificity and BBB penetration of 1 with CEP-1347 (2). Compound 1 is well tolerated, with excellent in vivo activity in HAND models, and is under investigation for further development. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

Fu, Liqiang et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2012 | CAS: 110568-64-4

6-Nitroisoindolin-1-one (cas: 110568-64-4) belongs to indole 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 6-Nitroisoindolin-1-one

Design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates was written by Fu, Liqiang;Liu, Xin;Ling, Chenyu;Cheng, Jianjun;Guo, Xingsheng;He, Huili;Ding, Shi;Yang, Yushe. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Recommanded Product: 6-Nitroisoindolin-1-one This article mentions the following:

We report herein the design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates based on the structure of SB-222734. For example, reacting benzoates I (R¹ = H, MeO, NO₂, R² = H, F, NO₂, R⁹ = H) with N-bromosuccinimide gave the brominated compounds I (R⁹ = Br), which cyclized to give isoindolinones II. II were then coupled with 4-epi-mutilin 14-chloroformate III and treated with a saturated solution of ZnCl₂ in concentrated HCl resulting in a reverse 1,5-hydride shift to afford desired products IV. The antibacterial activities of these newly synthesized compounds were also evaluated and compared with linezolid and retapamulin. Results showed that most of the target compounds exhibit good potency in inhibiting the growth of Gram-pos. bacteria including Methicillin-susceptible Staphylococcus aureus MSSA (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. aureus MRSA (MIC: 0.0625-2 μg/mL), Methicillin-susceptible Staphylococcus epidermidis MSSE (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. epidermidis MRSE (MIC: 0.0625-2 μg/mL), and Streptococcus pneumonia (MIC: 0.0625-4 μg/mL). In particular, three remarkable compounds of this series IV (R¹ = NH₂, R² = H; R¹ = H, R² = NH₂) and isoquinolinyl derivative V exhibited comparable in vitro antibacterial profiles to that of retapamulin. In the experiment, the researchers used many compounds, for example, 6-Nitroisoindolin-1-one (cas: 110568-64-4Recommanded Product: 6-Nitroisoindolin-1-one).

Li, Jianxiao et al. published their research in Journal of Organic Chemistry in 2016 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 6-Nitro-1H-indole

Palladium-catalyzed oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur was written by Li, Jianxiao;Li, Chunsheng;Yang, Shaorong;An, Yanni;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Journal of Organic Chemistry in 2016.Name: 6-Nitro-1H-indole This article mentions the following:

An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of 1-R²-2-R⁴-R³-indoles and 2-R⁴-6-R³-imidazo[1,2-a]pyridines with aryl boronic acids and elemental sulfur for the synthesis of 3-sulfenylindole derivatives I and II, resp. (R¹ = H, alkyl, MeO, halo, CN; R² = H, Me, PhCH₂; R³ = H, halo, alkyl, MeO, NO₂; R⁴ = H, Me, CO₂Et, Ph) is disclosed. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).