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Journal articles on the topic 'Tryptanthrin'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Frolova, Svetlana G., Ksenia M. Klimina, Ravinder Kumar, Aleksey A. Vatlin, Deepak B. Salunke, Pravin Kendrekar, Valery N. Danilenko, and Dmitry A. Maslov. "Identification of Mutations Conferring Tryptanthrin Resistance to Mycobacterium smegmatis." Antibiotics 10, no. 1 (December 23, 2020): 6. http://dx.doi.org/10.3390/antibiotics10010006.

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Tuberculosis (TB), caused by Mycobacterium tuberculosis, is a global burden, responsible for over 1 million deaths annually. The emergence and spread of drug-resistant M. tuberculosis strains (MDR-, XDR- and TDR-TB) is the main challenge in global TB-control, requiring the development of novel drugs acting on new biotargets, thus able to overcome the drug-resistance. Tryptanthrin is a natural alkaloid, with great therapeutic potential due to its simple way of synthesis and wide spectrum of biological activities including high bactericidal activity on both drug-susceptible and MDR M. tuberculosis strains. InhA was suggested as the target of tryptanthrins by in silico modeling, making it a promising alternative to isoniazid, able to overcome drug resistance provided by katG mutations. However, neither the mechanism of action of tryptanthrin nor the mechanism of resistance to tryptanthrins was ever confirmed in vitro. We show that the MmpS5-MmpL5 efflux system is able to provide resistance to tryptanthrins using an in-house test-system. Comparative genomic analysis of spontaneous tryptanthrin-resistant M. smegmatis mutants showed that mutations in MSMEG_1963 (EmbR transcriptional regulator) lead to a high-level resistance, while those in MSMEG_5597 (TetR transcriptional regulator) to a low-level one. Mutations in an MFS transporter gene (MSMEG_4427) were also observed, which might be involved in providing a basal level of tryptanthrins-resistance.

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2

Krivogorsky, Bogdana, Peter Grundt, Robert Yolken, and Lorraine Jones-Brando. "Inhibition of Toxoplasma gondii by Indirubin and Tryptanthrin Analogs." Antimicrobial Agents and Chemotherapy 52, no. 12 (September 29, 2008): 4466–69. http://dx.doi.org/10.1128/aac.00903-08.

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ABSTRACT New drugs are needed for treatment of Toxoplasma gondii infections. We tested derivatives of principles found in Isatis indigotica for in vitro efficacy against T. gondii infection. Indirubin-3′-oxime analogs showed modest micromolar activity, while tryptanthrin derivatives displayed 50% inhibitory doses in the low nanomolar range. Tryptanthrins have potential as anti-Toxoplasma infection therapeutics.

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3

Zhu, Xingang, Xuelian Zhang, Guo Ma, Junkai Yan, Honghai Wang, and Qing Yang. "Transport Characteristics of Tryptanthrin and its Inhibitory Effect on P-gp and MRP2 in Caco-2 Cells." Journal of Pharmacy & Pharmaceutical Sciences 14, no. 3 (August 8, 2011): 325. http://dx.doi.org/10.18433/j3501w.

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Purpose. Tryptanthrin, an indole quinazoline alkaloid with multiple medical activities, has been recently under preclinical development as an anti-tuberculosis and anti-tumor drug. The aims of this study are to characterize the intestinal transport of tryptanthrin in Caco-2 cells, to determine whether P-glycoprotein (P-gp) and multidrug resistance-associated protein 2 (MRP2) are involved in this issue, and to evaluate the potential influence of tryptanthrin on the function of P-gp and MRP2. Methods. Transport assays of tryptanthrin were performed in Caco-2 monolayers with or without the supplement of P-gp and MRP2 inhibitors. Transport assays of P-gp and MRP2 substrates were also performed in the presence of tryptanthrin. The effect of tryptanthrin on the expression of P-gp and MRP2 was analyzed by reverse transcriptase-PCR. Results. Both absorption and secretion of tryptanthrin were concentration-independent at a low concentration range of 0.8–20 µM. The apparent permeability (Papp) for the apical (AP) to basolateral (BL) was 6.138 ± 0.291 × 10-5. The ratio of Papp (BL→AP) to Papp (AP→BL) was 0.77, suggesting greater permeability in the absorptive direction. Both the P-gp inhibitor, verapamil, and the MRP2 inhibitor, glibenclamide, didn’t affect the efflux transport of tryptanthrin. The efflux transport of the P-gp substrate, digoxin, and the MRP2 substrate, pravastatin sodium, decreased when tryptanthrin was present. However, tryptanthrin didn’t change the expression of P-gp and MRP2. Conclusions. Tryptanthrin was well absorbed across the Caco-2 monolayers, and its transepithelial transports were dominated by passive diffusion. Tryptanthrin was not a substrate, but a potential inhibitor of P-gp and MRP2. This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.

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4

Zeng, Qingfang, Cairong Luo, Junlae Cho, Donna Lai, Xiangchun Shen, Xiaoyan Zhang, and Wei Zhou. "Tryptanthrin exerts anti-breast cancer effects both in vitro and in vivo through modulating the inflammatory tumor microenvironment." Acta Pharmaceutica 71, no. 2 (November 4, 2020): 245–66. http://dx.doi.org/10.2478/acph-2021-0020.

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Abstract Tryptanthrin is an indole quinazoline alkaloid from the indigo-bearing plants, such as Isatis indigotica Fort. Typically, this natural compound shows a variety of pharmacological activities such as antitumor, antibacterial, anti-inflammatory and antioxidant effects. This study was conducted to assess the antitumor activity of tryptanthrin in breast cancer models both in vitro and in vivo, and to explore the important role of the inflammatory tumor microenvironment (TME) in the antitumor effects of tryptanthrin. Human breast adenocarcinoma MCF-7 cells were used to assess the antitumor effect of tryptanthrin in vitro. MTT assay and colony formation assay were carried out to monitor the antiproliferative effect of tryptanthrin (1.56~50.0 μmol L−1) on inhibiting the proliferation and colony formation of MCF-7 cells, respectively. The migration and invasion of MCF-7 cells were evaluated by wound healing assay and Transwell chamber assay, respectively. Moreover, the 4T1 murine breast cancer model was established to examine the pharmacological activity of tryptanthrin, and three groups with different doses of tryptanthrin (25, 50 and 100 mg kg−1) were set in study. Additionally, tumor volumes and organ coefficients were measured and calculated. After two weeks of tryptanthrin treatment, samples from serum, tumor tissue and different organs from tumor-bearing mice were collected, and the enzyme-linked immunosorbent assay (ELISA) was performed to assess the regulation of inflammatory molecules in mouse serum. Additionally, pathological examinations of tumor tissues and organs from mice were evaluated through hematoxylin and eosin (H&E) staining. The expression of inflammatory proteins in tumor tissues was measured by immunohistochemistry (IHC) and Western blotting. Tryptanthrin inhibited the proliferation, migration and invasion of MCF-7 cells, up-regulated the protein level of E-cadherin, and down-regulated those of MMP-2 and Snail, as suggested by the MCF-7 cell experiment. According to the results from in vivo experiment, tryptanthrin was effective in inhibiting tumor growth, and it showed favorable safety without inducing the fluctuations of body mass and organ coefficient (p > 0.05). In addition, tryptanthrin also suppressed the expression levels of NOS1, COX-2 and NF-κB in mouse tumor tissues, and regulated those of IL-2, IL-10 and TNF-α in the serum of tumor cells-transplanted mice. Tryptanthrin exerted its anti-breast cancer activities through modulating the inflammatory TME both in vitro and in vivo.

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5

Tripathi, Vishwa Deepak. "Natural Product Inspired Synthesis of Tryptanthrin Analogues as Potential Antimalarial Agents." Asian Journal of Organic & Medicinal Chemistry 5, no. 4 (December 31, 2020): 348–54. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p302.

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A new series of tryptanthrin analogues have been synthesized as potential antimalarial molecules. Synthesis of tryptanthrin aminoalkyl derivatives have been achieved via alkylation of oxime functionality of tryptanthrin derivatives by various alkyl amino pharmacophoric chains. 21-Membered small library of tryptanthrin aminoalkyl analogues were synthesized with variation in both parent natural alkaloid and in amino alkyl side chains. Synthesized compounds were fully characterized with 1H & 13C NMR, IR spectroscopy. Further all the members were screened for their antimalarial potential against Plasmoum falciparum in both sensitive (3D7) and in resistant (k1) strains. Most of the screened compounds were exhibited potent antimalarial activity in both strains. Compounds (5m, 3c and 5l) having nitro group at the 8 position in tryptanthrin framework were most promising compounds in series (IC50 = 10 nm) with IC50 value as low as 10 nm comparable to chloroquine. These compounds were also tested for their toxic effect and found to be highly safe with very high value of SI index.

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6

Tsai, Yu-Chi, Chia-Lin Lee, Hung-Rong Yen, Young-Sheng Chang, Yu-Ping Lin, Su-Hua Huang, and Cheng-Wen Lin. "Antiviral Action of Tryptanthrin Isolated from Strobilanthes cusia Leaf against Human Coronavirus NL63." Biomolecules 10, no. 3 (February 27, 2020): 366. http://dx.doi.org/10.3390/biom10030366.

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Strobilanthes cusia (Nees) Kuntze is a Chinese herbal medicine used in the treatment of respiratory virus infections. The methanol extract of S. cusia leaf contains chemical components such as β-sitosterol, indirubin, tryptanthrin, betulin, indigodole A, and indigodole B that have diverse biological activities. However, the antiviral action of S. cusia leaf and its components against human coronavirus remains to be elucidated. Human coronavirus NL63 infection is frequent among immunocompromised individuals, young children, and in the elderly. This study investigated the anti-Human coronavirus NL63 (HCoV-NL63) activity of the methanol extract of S. cusia leaf and its major components. The methanol extract of S. cusia leaf effectively inhibited the cytopathic effect (CPE) and virus yield (IC50 = 0.64 μg/mL) in HCoV-NL63-infected cells. Moreover, this extract potently inhibited the HCoV-NL63 infection in a concentration-dependent manner. Among the six components identified in the methanol extract of S. cusia leaf, tryptanthrin and indigodole B (5aR-ethyltryptanthrin) exhibited potent antiviral activity in reducing the CPE and progeny virus production. The IC50 values against virus yield were 1.52 μM and 2.60 μM for tryptanthrin and indigodole B, respectively. Different modes of time-of-addition/removal assay indicated that tryptanthrin prevented the early and late stages of HCoV-NL63 replication, particularly by blocking viral RNA genome synthesis and papain-like protease 2 activity. Notably, tryptanthrin (IC50 = 0.06 μM) and indigodole B (IC50 = 2.09 μM) exhibited strong virucidal activity as well. This study identified tryptanthrin as the key active component of S. cusia leaf methanol extract that acted against HCoV-NL63 in a cell-type independent manner. The results specify that tryptanthrin possesses antiviral potential against HCoV-NL63 infection.

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7

Batanero, Belen, and Fructuoso Barba. "Electrosynthesis of tryptanthrin." Tetrahedron Letters 47, no. 47 (November 2006): 8201–3. http://dx.doi.org/10.1016/j.tetlet.2006.09.130.

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8

Costa, Fabio Luiz Paranhos, Sidnei Bessa de Oliveira Fernandes, Catharina Eccard Fingolo, Fabio Boylan, Antônio M. de J. Chaves Neto, Gunar Vingre da Silva Mota, Breno Almeida Soares, Marcelo Ricardo Souza Siqueira, and Thaís Forest Giacomello. "Experimental and Theoretical Nuclear Magnetic Resonance Data from Tryptanthrin, an Alkaloid with Potential Activity Against Human Coronavirus." Advanced Science, Engineering and Medicine 12, no. 7 (July 1, 2020): 963–69. http://dx.doi.org/10.1166/asem.2020.2638.

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Coronaviruses belong to the subfamily Coronavirinae, which are large viruses with a single Ribonucleic acid tape and a nucleocapsid. In a recent study it was found that the molecule of tryptanthrin has antiviral potential against human coronavirus NL63. In this work, we used a combination of theoretical techniques with experimental nuclear magnetic resonance data to assist in the structural characterization of the Tryptanthrin molecule. Tryptanthrin was extracted from Couroupita guianensis leaves. The theoretical calculations of hydrogen-1, homonuclear spin–spin coupling constants and the quantum theory of atoms in molecules were performed employing density functional theory. Our results show that the hydrogen-1 chemical shifts calculated at the gaseous phase and solvent presented similar performance. The quantum theory of atoms in molecules calculations was able to quantify and qualify bonded interactions based on five topological parameters obtained at the analyzed bond critical point to tryptanthrin molecule. We obtained a satisfactory correlation between tryptanthrin delocalization index values and its experimental and calculated proton–proton coupling constants. In conclusion, the theoretical techniques used in this work in combination with NMR experimental data can be a useful tool in aiding the structural determination of organic compounds.

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9

Zhong, Yi-ning, Yan Zhang, Yun-qiong Gu, Shi-yun Wu, Wen-ying Shen, and Ming-xiong Tan. "NovelFeIIandCoIIComplexes of Natural Product Tryptanthrin: Synthesis and Binding with G-Quadruplex DNA." Bioinorganic Chemistry and Applications 2016 (2016): 1–7. http://dx.doi.org/10.1155/2016/5075847.

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Tryptanthrin is one of the most important members of indoloquinoline alkaloids. We obtained this alkaloid fromIsatis. Two novelFeIIandCoIIcomplexes of tryptanthrin were first synthesized. Single-crystal X-ray diffraction analyses show that these complexes display distorted four-coordinated tetrahedron geometry via two heterocyclic nitrogen and oxygen atoms from tryptanthrin ligand. Binding with G-quadruplex DNA properties revealed that both complexes were found to exhibit significant interaction with G-quadruplex DNA. This study may potentially serve as the basis of future rational design of metal-based drugs from natural products that target the G-quadruplex DNA.

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10

Liao, Fu-Min, Yun-Lin Liu, Jin-Sheng Yu, Feng Zhou, and Jian Zhou. "An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin." Organic & Biomolecular Chemistry 13, no. 33 (2015): 8906–11. http://dx.doi.org/10.1039/c5ob01125f.

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We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This represents the first modification of tryptanthrin by a fluoroalkyl group, which is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

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11

Scovill, John, Elizabeth Blank, Michael Konnick, Elizabeth Nenortas, and Theresa Shapiro. "Antitrypanosomal Activities of Tryptanthrins." Antimicrobial Agents and Chemotherapy 46, no. 3 (March 2002): 882–83. http://dx.doi.org/10.1128/aac.46.3.882-883.2002.

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ABSTRACT New drugs and molecular targets are needed against Trypanosoma brucei, the protozoan that causes African sleeping sickness. Tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), a traditional antifungal agent, and 11 analogs were tested against T. brucei in vitro. The greatest activity was conferred by electron-withdrawing groups in the 8 position of the tryptanthrin ring system; the most potent compound had a 50% effective concentration of 0.40 μM.

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12

Liao, Huiwu, Xiangjun Peng, Dan Hu, Xianyun Xu, Panpan Huang, Qian Liu, and Liangxian Liu. "CoCl2-promoted TEMPO oxidative homocoupling of indoles: access to tryptanthrin derivatives." Organic & Biomolecular Chemistry 16, no. 31 (2018): 5699–706. http://dx.doi.org/10.1039/c8ob01216d.

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13

Hou, Hong, Hengxue Li, Ying Han, and Chaoguo Yan. "Synthesis of visible-light mediated tryptanthrin derivatives from isatin and isatoic anhydride under transition metal-free conditions." Organic Chemistry Frontiers 5, no. 1 (2018): 51–54. http://dx.doi.org/10.1039/c7qo00740j.

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14

Brandão, Pedro, Carolina Marques, Eugénia Pinto, Marta Pineiro, and Anthony J. Burke. "Petasis adducts of tryptanthrin – synthesis, biological activity evaluation and druglikeness assessment." New Journal of Chemistry 45, no. 32 (2021): 14633–49. http://dx.doi.org/10.1039/d1nj02079j.

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15

Kawakami, Jun, Chica Osanai, Shun Ohta, and Shunji Ito. "Solid-State Fluorescence of Tryptanthrin Analogs." Transactions of the Materials Research Society of Japan 46, no. 1 (March 1, 2021): 45–48. http://dx.doi.org/10.14723/tmrsj.46.45.

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16

Zhao, Li Fang, Yan Cheng Liu, Qi Pin Qin, Wen Zu Ya, and Hai Chun Duan. "Tryptanthrin Sulfonate: Crystal Structure, Cytotoxicity and DNA Binding Studies." Advanced Materials Research 554-556 (July 2012): 1694–99. http://dx.doi.org/10.4028/www.scientific.net/amr.554-556.1694.

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Tryptanthrin (TPT), which is an indoloquinazoline alkaloid with multiple biological activities, was studied on its sulfonation in order to increase its water solubility. An 8-substituted tryptanthrin sulfonate (TPTS) was synthesized and structurally characterized by IR, 1H-NMR, ESI-MS, as well as X-ray single crystal diffraction analysis. The interactional mechanism of TPTS with calf thymus DNA (ctDNA) was further studied by UV spectroscopy and DNA viscosity experiment. The addition of ctDNA into the TPTS solution induced moderate hypochromicity on its electronic absorption spectrum, by which an intrinsic binding constant of 1.10×104 M-1 was achieved. While addition of TPTS caused significant increasement on the viscosity of ctDNA solution. The results suggest that TPTS interacts with ctDNA mainly by intercalative binding mode.

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17

Tucker, Ashli M., and Peter Grundt. "The chemistry of tryptanthrin and its derivatives." Arkivoc 2012, no. 1 (July 29, 2012): 546–69. http://dx.doi.org/10.3998/ark.5550190.0013.113.

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18

Deryabin, P. I., T. V. Moskovkina, A. V. Bukreev, A. V. Andina, and A. V. Gerasimenko. "Synthesis of Spiroheterocyclic Oxygen-Containing Tryptanthrin Derivatives." Russian Journal of Organic Chemistry 54, no. 4 (April 2018): 622–25. http://dx.doi.org/10.1134/s1070428018040176.

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19

Kawakami, Jun, Noriyuki Matsushima, Yuta Ogawa, Hiroko Kakinami, Akio Nakane, Haruo Kitahara, Masahiko Nagaki, and Shunji Ito. "Antibacterial and Antifungal Activities of Tryptanthrin Derivatives." Transactions of the Materials Research Society of Japan 36, no. 4 (2011): 603–6. http://dx.doi.org/10.14723/tmrsj.36.603.

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20

Kaur, Ramandeep, Sundeep Kaur Manjal, Ravindra K. Rawal, and Kapil Kumar. "Recent synthetic and medicinal perspectives of tryptanthrin." Bioorganic & Medicinal Chemistry 25, no. 17 (September 2017): 4533–52. http://dx.doi.org/10.1016/j.bmc.2017.07.003.

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21

Guo, Jincheng, Yanan Hao, Gang Li, Ziwen Wang, Yuxiu Liu, Yongqiang Li, and Qingmin Wang. "Efficient synthesis of SCF3-substituted tryptanthrins by a radical tandem cyclization." Organic & Biomolecular Chemistry 18, no. 10 (2020): 1994–2001. http://dx.doi.org/10.1039/d0ob00233j.

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An efficient strategy for synthesis of SCF₃-substituted tryptanthrin derivatives was developed with AgSCF₃/K₂S₂O₈-promoted radical trifluoromethylthiolation/cyclization cascade reaction as key step.

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22

Boitsov, Vitali, Alexander Stepakov, Alexander Filatov, Nickolay Knyazev, Stanislav Shmakov, Alexey Bogdanov, Mikhail Ryazantsev, et al. "Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes." Synthesis 51, no. 03 (October 10, 2018): 713–29. http://dx.doi.org/10.1055/s-0037-1611059.

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A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.

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23

Kumar, Atul, Vishwa Deepak Tripathi, and Promod Kumar. "β-Cyclodextrin catalysed synthesis of tryptanthrin in water." Green Chem. 13, no. 1 (2011): 51–54. http://dx.doi.org/10.1039/c0gc00523a.

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24

Wu, Jie, Chao Huang, Guo-Qiang Li, Hai-Yan Tian, and Ren-Wang Jiang. "(Nitrato-κ2O,O′)bis(tryptanthrin-κN)silver(I)." Acta Crystallographica Section E Structure Reports Online 68, no. 2 (January 21, 2012): m185—m186. http://dx.doi.org/10.1107/s1600536812001821.

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25

Zhang, Shengnan, Fangfei Qi, Xin Fang, Dan Yang, Hairong Hu, Qiang Huang, Chunxiang Kuang, and Qing Yang. "Tryptophan 2,3-dioxygenase inhibitory activities of tryptanthrin derivatives." European Journal of Medicinal Chemistry 160 (December 2018): 133–45. http://dx.doi.org/10.1016/j.ejmech.2018.10.017.

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26

Seifert, K., and W. U nger. "Insecticidal and Fungicidal Compounds from Isatis tinctoria." Zeitschrift für Naturforschung C 49, no. 1-2 (February 1, 1994): 44–48. http://dx.doi.org/10.1515/znc-1994-1-208.

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Tryptanthrin (1), indole-3-acetonitrile (2) and p-coumaric acid methylester (3) were isolated from the aerial parts of Isatis tinctoria L. The compounds show insecticidal and antifeedant activity against termites (Reticulitermis santonensis), insect preventive and control activity against larvae of the house longhorn beetle (Hylotrupes bajulus) and fungicidal activity against the brown-rot fungus (Coniophora puteana).

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27

Rai, Byanju, Ratnakar Dutt Shukla, and Atul Kumar. "Zinc oxide-NP catalyzed direct indolation of in situ generated bioactive tryptanthrin." Green Chemistry 20, no. 4 (2018): 822–26. http://dx.doi.org/10.1039/c7gc03479b.

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A ZnO-NP catalyzed direct indolation of in situ generated tryptanthrin via C–H functionalization and C–C bond formation has been developed. This novel and greener approach has been effectively utilized to accomplish the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b] quinazolin-12(6H)-one derivatives in good to excellent yields with high product selectivity.

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Tucker, Ashli M., and Peter Grundt. "ChemInform Abstract: The Chemistry of Tryptanthrin and Its Derivatives." ChemInform 43, no. 43 (September 27, 2012): no. http://dx.doi.org/10.1002/chin.201243254.

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Deryabin, P. I., T. V. Moskovkina, L. S. Shevchenko, and A. I. Kalinovskii. "Synthesis and antimicrobial activity of tryptanthrin adducts with ketones." Russian Journal of Organic Chemistry 53, no. 3 (March 2017): 418–22. http://dx.doi.org/10.1134/s1070428017030174.

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30

Danz, Henning, Stefka Stoyanova, Olivier A. Thomet, Hans-Uwe Simon, Gerd Dannhardt, Holger Ulbrich, and Matthias Hamburger. "Inhibitory Activity of Tryptanthrin on Prostaglandin and Leukotriene Synthesis." Planta Medica 68, no. 10 (October 2002): 875–80. http://dx.doi.org/10.1055/s-2002-34922.

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31

Wang, Chen, Lianpeng Zhang, Anni Ren, Ping Lu, and Yanguang Wang. "Cu-Catalyzed Synthesis of Tryptanthrin Derivatives from Substituted Indoles." Organic Letters 15, no. 12 (June 7, 2013): 2982–85. http://dx.doi.org/10.1021/ol401144m.

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32

Han, Na-Ra, Phil-Dong Moon, Hyung-Min Kim, and Hyun-Ja Jeong. "Tryptanthrin ameliorates atopic dermatitis through down-regulation of TSLP." Archives of Biochemistry and Biophysics 542 (January 2014): 14–20. http://dx.doi.org/10.1016/j.abb.2013.11.010.

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33

Onambele, Liliane Abodo, Herbert Riepl, Rainer Fischer, Gabriele Pradel, Aram Prokop, and Makoah Nigel Aminake. "Synthesis and evaluation of the antiplasmodial activity of tryptanthrin derivatives." International Journal for Parasitology: Drugs and Drug Resistance 5, no. 2 (August 2015): 48–57. http://dx.doi.org/10.1016/j.ijpddr.2015.03.002.

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34

Kumar, Atul, Vishwa Deepak Tripathi, and Promod Kumar. "ChemInform Abstract: β-Cyclodextrin Catalyzed Synthesis of Tryptanthrin in Water." ChemInform 42, no. 22 (May 5, 2011): no. http://dx.doi.org/10.1002/chin.201122210.

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35

Abe, Takumi, and Masaru Terasaki. "Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade." Helvetica Chimica Acta 101, no. 2 (January 22, 2018): e1700284. http://dx.doi.org/10.1002/hlca.201700284.

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36

Yu, Sung-tsai, Ji-wang Chern, Tzer-ming Chen, Yi-fan Chiu, Hui-ting Chen, and Yen-hui Chen. "Cytotoxicity and reversal of multidrug resistance by tryptanthrin-derived indoloquinazolines." Acta Pharmacologica Sinica 31, no. 2 (February 2010): 259–64. http://dx.doi.org/10.1038/aps.2009.198.

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37

Recio, María-Carmen, Miguel Cerdá-Nicolás, Olivier Potterat, Matthias Hamburger, and José-Luis Ríos. "Anti-Inflammatory and Antiallergic Activityin vivoof LipophilicIsatis tinctoriaExtracts and Tryptanthrin." Planta Medica 72, no. 06 (April 2006): 539–46. http://dx.doi.org/10.1055/s-2006-931562.

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38

Jahng, Yurngdong. "Progress in the studies on tryptanthrin, an alkaloid of history." Archives of Pharmacal Research 36, no. 5 (March 31, 2013): 517–35. http://dx.doi.org/10.1007/s12272-013-0091-9.

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39

Jao, Chen-Wei, Wei-Chih Lin, Yao-Ting Wu, and Pei-Lin Wu. "Isolation, Structure Elucidation, and Synthesis of Cytotoxic Tryptanthrin Analogues fromPhaius mishmensis." Journal of Natural Products 71, no. 7 (July 2008): 1275–79. http://dx.doi.org/10.1021/np800064w.

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40

Ishihara, Tatsuya, Keizo Kohno, Shimpei Ushio, Kanso Iwaki, Masao Ikeda, and Masashi Kurimoto. "Tryptanthrin inhibits nitric oxide and prostaglandin E2 synthesis by murine macrophages." European Journal of Pharmacology 407, no. 1-2 (October 2000): 197–204. http://dx.doi.org/10.1016/s0014-2999(00)00674-9.

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41

Yu, Sung-Tsai, Tzer-Ming Chen, Shih-Yun Tseng, and Yen-Hui Chen. "Tryptanthrin inhibits MDR1 and reverses doxorubicin resistance in breast cancer cells." Biochemical and Biophysical Research Communications 358, no. 1 (June 2007): 79–84. http://dx.doi.org/10.1016/j.bbrc.2007.04.107.

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42

Wang, Chen, Lianpeng Zhang, Anni Ren, Ping Lu, and Yanguang Wang. "ChemInform Abstract: Cu-Catalyzed Synthesis of Tryptanthrin Derivatives from Substituted Indoles." ChemInform 44, no. 47 (November 4, 2013): no. http://dx.doi.org/10.1002/chin.201347158.

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43

Duca, Gheorghe, Serghei Pogrebnoi, Veaceslav Boldescu, Fatma Aksakal, Andrei Uncu, Vladimir Valica, Livia Uncu, Simona Negres, Florica Nicolescu, and Fliur Macaev. "Tryptanthrin Analogues as Inhibitors of Enoyl-acyl Carrier Protein Reductase: Activity against Mycobacterium tuberculosis, Toxicity, Modeling of Enzyme Binding." Current Topics in Medicinal Chemistry 19, no. 8 (June 3, 2019): 609–19. http://dx.doi.org/10.2174/1568026619666190304125740.

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Abstract:

Background: High numbers of infection with resistant forms of Micobacterium tuberculosis (Mtb) contribute to a constant growing demand in new highly active and effective therapeutics. Current drug discovery efforts directed towards new antituberculosis agents include the development of new inhibitors of enoyl-acyl carrier protein reductase (InhA) that do not require activation by the specific enzymes. Tryptanthrin is a known inhibitor of Mtb InhA and its analogues are investigated as potential agents with antimycobacterial efficiency. Objective: The main objective of the presented research was to develop a new group of tryptanthrin analogues with good inhibition properties against Mtb. Methods: Synthesis of new derivatives of 5H-[1,3,4]thiadiazolo[2,3- b]quinazolin-5-one and evaluation of their activity against Mtb, as well as acute and chronic toxicity studies were carried out. Molecular modeling studies were performed to investigate the binding mechanisms of the synthesized ligands with InhA. Binding energies and non-covalent interactions stabilizing the ligand-receptor complexes were obtained from the results of molecular docking. Results: The most active compound in the obtained series, 2-(propylthio)-5H-[1,3,4]thiadiazolo[2,3- b]quinazolin-5-one, exhibited the superior inhibition activity (up to 100%) against mycobacterial growth at MIC 6.5 µg/mL, showed good affinity to the InhA enzyme in docking studies and demonstrated a very low per oral toxicity in animals falling under the category 5 according to GHS classification. Conclusions: 2-(propylthio)-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-one can be further explored for the development of a new series of compounds active against Mtb.

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44

Eguchi, Shoji, Hisato Takeuchi, and Yuji Matsushita. "Short-step Synthesis of Rutecarpine and Tryptanthrin via Intramoleculer Aza-wittig Reaction." HETEROCYCLES 33, no. 1 (1992): 153. http://dx.doi.org/10.3987/com-91-s62.

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45

Motoki, Takahiro, Yoichiro Takami, Yasuyuki Yagi, Akihiro Tai, Itaru Yamamoto, and Eiichi Gohda. "Inhibition of Hepatocyte Growth Factor Induction in Human Dermal Fibroblasts by Tryptanthrin." Biological & Pharmaceutical Bulletin 28, no. 2 (2005): 260–66. http://dx.doi.org/10.1248/bpb.28.260.

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46

Nelson, Amber C., Emily S. Kalinowski, Taylor L. Jacobson, and Peter Grundt. "Formation of tryptanthrin compounds upon Oxone-induced dimerization of indole-3-carbaldehydes." Tetrahedron Letters 54, no. 50 (December 2013): 6804–6. http://dx.doi.org/10.1016/j.tetlet.2013.09.124.

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47

Chan, Hoi-Ling, Hon-Yan Yip, Nai-Ki Mak, and Kwok-Nam Leung. "Modulatory Effects and Action Mechanisms of Tryptanthrin on Murine Myeloid Leukemia Cells." Cellular & Molecular Immunology 6, no. 5 (October 2009): 335–42. http://dx.doi.org/10.1038/cmi.2009.44.

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48

Sultan, Shaista, Vivek Gupta, and Bhahwal Ali Shah. "Photoredox-Catalyzed Isatin Reactions: Access to Dibenzo-1,7-Naphthyridine Carboxylate and Tryptanthrin." ChemPhotoChem 1, no. 4 (March 9, 2017): 120–24. http://dx.doi.org/10.1002/cptc.201700028.

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Liao, Xuemei, Xuelin Zhou, Nai-ki Mak, and Kwok-nam Leung. "Tryptanthrin Inhibits Angiogenesis by Targeting the VEGFR2-Mediated ERK1/2 Signalling Pathway." PLoS ONE 8, no. 12 (December 16, 2013): e82294. http://dx.doi.org/10.1371/journal.pone.0082294.

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Kawakami, Jun, Takuma Kadowaki, Mari Ikeda, Yoichi Habata, Shunji Ito, and Haruo Kitahara. "Spectral Characteristics of Highly Fluorescent 2-(N,N-dimethylamino)tryptanthrin." Transactions of the Materials Research Society of Japan 41, no. 2 (2016): 143–46. http://dx.doi.org/10.14723/tmrsj.41.143.

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