Indole Building Blocks

Lei, Lin-Sheng’s team published research in Advanced Synthesis & Catalysis in 2020 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Recommanded Product: 399-52-0

《Al(OTf)3-Catalyzed Tandem Coupling Reaction between N,N-Disubstituted Aminomalonitriles and Substituted Arenes: a Synthesis of 1-Cyano-bisindolylmethane Analogues》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Lei, Lin-Sheng; Wang, Bo-Wen; Jin, Da-Ping; Gao, Zhu-Peng; Huan-Liang; Wang, Shao-Hua; Xu, Xue-Tao; Zhang, Kun; Zhang, Xiao-Yun. Recommanded Product: 399-52-0 The article mentions the following:

A synthesis of 1-cyano-bisarylmethane analogs via an Al(OTf)3-catalyzed tandem coupling reaction between N,N-disubstituted aminomalonitriles and substituted arenes were developed. This method not only provided an alternative synthetic strategy for the synthesis of corresponding functional mols., but also enriches the volume of bisarylmethanes library to facilitate related functional studies. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 399-52-0)

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

Duan, Shengguo’s team published research in Advanced Synthesis & Catalysis in 2020 | CAS: 399-52-0

《Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles》 was written by Duan, Shengguo; An, Yuehui; Xue, Bing; Chen, Yidian; Zhang, Wan; Xu, Ze-Feng; Li, Chuan-Ying. Name: 5-Fluoro-1H-indole And the article was included in Advanced Synthesis & Catalysis in 2020. The article conveys some information:

Acyloxy-substituted α,β-unsaturated imines generated in-situ from triazoles acts as aza-[4C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system included operational simplicity, readily available substrates, construction of sterically demanding quaternary centers and convenient derivatization using triflate. The results came from multiple reactions, including the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Name: 5-Fluoro-1H-indole)

Shavit, Reut’s team published research in Plant Science (Shannon, Ireland) in 2022 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. 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.Safety of 1H-Indole

《The wheat dioxygenase BX6 is involved in the formation of benzoxazinoids in planta and contributes to plant defense against insect herbivores》 was written by Shavit, Reut; Batyrshina, Zhaniya S.; Yaakov, Beery; Florean, Matilde; Kollner, Tobias G.; Tzin, Vered. Safety of 1H-IndoleThis research focused onwheat dioxygenase benzoxazinoid insect herbivore plant defense; Aphid; Bread wheat; Caterpillar; Durum wheat; Herbivory; Triticum aestivum; Triticum turgidum; Two-spotted spider mite; Virus-induced gene silencing; Wild emmer wheat. The article conveys some information:

Benzoxazinoids are plant specialized metabolites with defense properties, highly abundant in wheat (Triticum), one of the world′s most important crops. The goal of our study was to characterize dioxygenase BX6 genes in tetraploid and hexaploid wheat genotypes and to elucidate their effects on defense against herbivores. Phylogenetic anal. revealed four BX6 genes in the hexaploid wheat T. aestivum, but only one ortholog was found in the tetraploid (T. turgidum) wild emmer wheat and the cultivated durum wheat. Transcriptome sequencing of durum wheat plants, damaged by either aphids or caterpillars, revealed that several BX genes, including TtBX6, were upregulated upon caterpillar feeding, relative to the undamaged control plants. A virus-induced gene silencing approach was used to reduce the expression of BX6 in T. aestivum plants, which exhibited both reduced transcript levels and reduced accumulation of different benzoxazinoids. To elucidate the effect of BX6 on plant defense, bioassays with different herbivores feeding on BX6-silenced leaves were conducted. The results showed that plants with silenced BX6 were more susceptible to aphids and the two-spotted spider mite than the control. Overall, our study indicates that wheat BX6 is involved in benzoxazinoid formation in planta and contributes to plant resistance against insect herbivores. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Safety of 1H-Indole)

Liao, Hui’s team published research in Organic & Biomolecular Chemistry in 2020 | CAS: 885518-25-2

6-Fluoro-1H-indol-4-amine(cas: 885518-25-2) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.HPLC of Formula: 885518-25-2

《Water-DMSO-promoted one-pot synthesis of two new series of dihydropyrrolo[2,3-h]quinolines》 was published in Organic & Biomolecular Chemistry in 2020. These research results belong to Liao, Hui; Zhu, Qiuhua. HPLC of Formula: 885518-25-2 The article mentions the following:

Here, two new series of dihydropyrrolo[2,3-h]quinolines I (R1 = Me, Et, t-Bu; R2 = H, F, Cl; R3 = H, Me; R4 = C6H5, 4-FC6H4, 4-MeC6H4, etc.) with more substituents on the quinoline ring were efficiently synthesized via catalyst-free three-component reaction (3CR) of but-2-ynedioates, 4-aminoindoles and aldehydes or isatins in a DMSO-water (volume ratio: 2.5 : 1) mixture in moderate to good yields. A possible mechanism was proposed based on the crucial and promoted effects of water and DMSO in the 3CR, resp. In addition, it was found that dihydropyrrolo[2,3-h]quinolines could be quant. oxidized into new pyrrolo[2,3-h]quinolines at room temperature using Cu(NO3)2 as an oxidant. This work affords efficient synthesis methods for constructing a library of new pyrrolo[2,3-h]quinolines and is expected to promote the research on the bioactivities of pyrrolo[2,3-h]quinolines. In the part of experimental materials, we found many familiar compounds, such as 6-Fluoro-1H-indol-4-amine(cas: 885518-25-2HPLC of Formula: 885518-25-2)

Agnihotri, Geetanjali’s team published research in Carbohydrate Research in 2005 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.COA of Formula: C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

COA of Formula: C22H25NO9SOn May 23, 2005, Agnihotri, Geetanjali; Tiwari, Pallavi; Misra, Anup Kumar published an article in Carbohydrate Research. The article was 《One-pot synthesis of per-O-acetylated thioglycosides from unprotected reducing sugars》. The article mentions the following:

A sequential per-O-acetylation and thioglycosidation of unprotected reducing sugars using a stoichiometric quantity of acetic anhydride and alkyl- or arylthiols is reported. These reactions, which are catalyzed by BF3·OEt2, together constitute an efficient one-pot method for the synthesis of acetylated thioglycosides. In the experimental materials used by the author, we found Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2COA of Formula: C22H25NO9S)

Biswas, Nandita’s team published research in Advanced Synthesis & Catalysis in 2020 | CAS: 120-72-9

《Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Biswas, Nandita; Sharma, Rahul; Srimani, Dipankar. Safety of 1H-Indole The article mentions the following:

Herein, we presented Ru-SNS complex that served as a useful catalyst for the synthesis of alkyl-indoles I [R1 = H, 2-Me, 5-OMe, etc.; R2 = H, Me; R3 = Me, Et, Bn, etc.] via C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcs. including cyclic alcs. as well as benzylic alcs. The selective synthesis of bisindolylmethane derivatives II [R4 = H, Me, Ph, etc.] was also achieved from the same set of indole and alc. just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcs. catalyzed by a Ru-complex via ‘borrowing hydrogen’ strategy was reported. This protocol provided an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Safety of 1H-Indole)

Schnute, Mark E’s team published research in Journal of Medicinal Chemistry in 2018-12-13 | 101083-92-5

Journal of Medicinal Chemistry published new progress about Autoimmune disease. 101083-92-5 belongs to class indole-building-block, and the molecular formula is C7H5N3O2, Recommanded Product: 5-Nitro-1H-pyrrolo[2,3-b]pyridine.

Schnute, Mark E.; Wennerstal, Mattias; Alley, Jennifer; Bengtsson, Martin; Blinn, James R.; Bolten, Charles W.; Braden, Timothy; Bonn, Tomas; Carlsson, Bo; Caspers, Nicole; Chen, Ming; Choi, Chulho; Collis, Leon P.; Crouse, Kimberly; Farnegardh, Mathias; Fennell, Kimberly F.; Fish, Susan; Flick, Andrew C.; Goos-Nilsson, Annika; Gullberg, Hjalmar; Harris, Peter K.; Heasley, Steven E.; Hegen, Martin; Hromockyj, Alexander E.; Hu, Xiao; Husman, Bolette; Janosik, Tomasz; Jones, Peter; Kaila, Neelu; Kallin, Elisabet; Kauppi, Bjorn; Kiefer, James R.; Knafels, John; Koehler, Konrad; Kruger, Lars; Kurumbail, Ravi G.; Kyne, Robert E.; Li, Wei; Lofstedt, Joakim; Long, Scott A.; Menard, Carol A.; Mente, Scot; Messing, Dean; Meyers, Marvin J.; Napierata, Lee; Noteberg, Daniel; Nuhant, Philippe; Pelc, Matthew J.; Prinsen, Michael J.; Rhonnstad, Patrik; Backstrom-Rydin, Eva; Sandberg, Johnny; Sandstrom, Maria; Shah, Falgun; Sjoberg, Maria; Sundell, Aron; Taylor, Alexandria P.; Thorarensen, Atli; Trujillo, John I.; Trzupek, John D.; Unwalla, Ray; Vajdos, Felix F.; Weinberg, Robin A.; Wood, David C.; Xing, Li; Zamaratski, Edouard; Zapf, Christoph W.; Zhao, Yajuan; Wilhelmsson, Anna; Berstein, Gabriel published the artcile< Discovery of 3-Cyano-N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide: A Potent, Selective, and Orally Bioavailable Retinoic Acid Receptor-Related Orphan Receptor C2 Inverse Agonist>, Recommanded Product: 5-Nitro-1H-pyrrolo[2,3-b]pyridine, the main research area is cyanophenylamido isobutyrylpiperidinyl trifluoromethyl pyrrolopyridine preparation retinoic acid receptor; retinoic acid receptor related orphan receptor C2 inverse agonist; cyanobenzamide isobutyrylpiperidinyl pyrrolopyridinyl trifluoromethyl preparation retinoic acid receptor.

The nuclear hormone receptor retinoic acid receptor-related orphan C2 (RORC2, also known as RORγt) is a promising target for the treatment of autoimmune diseases. A small mol., inverse agonist of the receptor is anticipated to reduce production of IL-17, a key proinflammatory cytokine. Through a high-throughput screening approach, authors identified a mol. displaying promising binding affinity for RORC2, inhibition of IL-17 production in Th17 cells, and selectivity against the related RORA and RORB receptor isoforms. Lead optimization to improve the potency and metabolic stability of this hit focused on two key design strategies, namely, iterative optimization driven by increasing lipophilic efficiency and structure-guided conformational restriction to achieve optimal ground state energetics and maximize receptor residence time. This approach successfully identified 3-cyano-N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide as a potent and selective RORC2 inverse agonist, demonstrating good metabolic stability, oral bioavailability, and the ability to reduce IL-17 levels and skin inflammation in a preclin. in vivo animal model upon oral administration.

Wang, Qing-Dong’s team published research in Synlett in 2017-12-31 | 4771-48-6

Synlett published new progress about Formylation, regioselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Related Products of 4771-48-6.

Wang, Qing-Dong; Zhou, Bin; Yang, Jin-Ming; Fang, Dong; Ren, Jiangmeng; Zeng, Bu-Bing published the artcile< Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air>, Related Products of 4771-48-6, the main research area is formylindole preparation green chem regioselective; indole formaldehyde formylation iron catalyst.

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles such as 2-phenyl-1H-indole, 6-fluoro-1H-indole, 1-methyl-1H-indole, etc. was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles such as 2-phenyl-1H-indole-3-carbaldehyde, 6-fluoro-1H-indole-3-carbaldehyde, 1-methyl-1H-indole-3-carbaldehyde, etc. in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Synlett published new progress about Formylation, regioselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Related Products of 4771-48-6.

Sellmer, Andreas’s team published research in European Journal of Medicinal Chemistry in 2020-05-01 | 101083-92-5

European Journal of Medicinal Chemistry published new progress about Acute myeloid leukemia. 101083-92-5 belongs to class indole-building-block, and the molecular formula is C7H5N3O2, Reference of 101083-92-5.

Sellmer, Andreas; Pilsl, Bernadette; Beyer, Mandy; Pongratz, Herwig; Wirth, Lukas; Elz, Sigurd; Dove, Stefan; Henninger, Sven Julian; Spiekermann, Karsten; Polzer, Harald; Klaeger, Susan; Kuster, Bernhard; Boehmer, Frank D.; Fiebig, Heinz-Herbert; Kraemer, Oliver H.; Mahboobi, Siavosh published the artcile< A series of novel aryl-methanone derivatives as inhibitors of FMS-like tyrosine kinase 3 (FLT3) in FLT3-ITD-positive acute myeloid leukemia>, Reference of 101083-92-5, the main research area is aryl methanone preparation FLT3 tyrosine kinase inhibitor antitumor human; Acute myeloid leukemia; FLT3; FLT3 D835Y; FLT3-ITD; Tyrosine kinase inhibitor.

Mutants of the FLT3 receptor tyrosine kinase (RTK) with duplications in the juxtamembrane domain (FLT3-ITD) act as drivers of acute myeloid leukemia (AML). Potent tyrosine kinase inhibitors (TKi) of FLT3-ITD entered clin. trials and showed a promising, but transient success due to the occurrence of secondary drug-resistant AML clones. A further caveat of drugs targeting FLT3-ITD is the co-targeting of other RTKs which are required for normal hematopoiesis. This is observed quite frequently. Therefore, novel drugs are necessary to treat AML effectively and safely. Recently bis(1H-indol-2-yl)methanones were found to inhibit FLT3 and PDGFR kinases. In order to optimize these agents novel derivatives of these methanones with various substituents were synthesized. Methanone I and its carbamate derivative II inhibit FLT3-ITD at least as potently as the TKi AC220 (quizartinib). Models indicate corresponding interactions of I and quizartinib with FLT3. The activity of I is accompanied by a high selectivity for FLT3-ITD.

Chen, Weiliang’s team published research in Chemistry – A European Journal in 2015 | 4771-48-6

Chemistry – A European Journal published new progress about [3+2] Cycloaddition reaction. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Chen, Weiliang; Xia, Yong; Lin, Lili; Yuan, Xiao; Guo, Songsong; Liu, Xiaohua; Feng, Xiaoming published the artcile< Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides>, Application In Synthesis of 4771-48-6, the main research area is indole furan furoindole preparation; N,N′-dioxide-metal complex; asymmetric synthesis; epoxides; indoles.

A highly efficient N,N’-dioxide-nickel(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes (i.e., epoxides) was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). Under optimized conditions the synthesis of the target compounds was achieved using (1R,1’R,2S,2’S)-1,1′-(1,3-propanediyl)bis[N-[2,4,6-tris(1-methylethyl)phenyl]-2-pyrrolidinecarboxamide] 1,1′-dioxide, perchloric acid nickel(2+) salt hexahydrate (nickel perchlorate hexahydrate) and 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide lithium salt (lithium triflimide) as ligand-catalyst combination. Starting materials included 3-(4-methylphenyl)-2,2-oxiranedicarboxylic acid di-Me ester and 1,3-dimethyl-1H-indole derivatives The title compounds thus formed included 1,3a,4,8b-tetrahydro-4,8b-dimethyl-1-(4-methylphenyl)-3H-furo[3,4-b]indole-3,3-dicarboxylic acid 3,3-di-Me ester and related substances.