(R)-5-((S)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one

ID: ALA196

Chembl Id: CHEMBL196

Max Phase: Approved

First Approval: 1985

Molecular Formula: C6H8O6

Molecular Weight: 176.12

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-keto-l-gulofuranolactone | Acidum ascorbicum | Ascoltin | Ascorbate | Ascorbic acid | Ascorbic acid, l- | Ascorbicum acidum | Cevitamic acid | L-ascorbate | L-ascorbic acid | Vitamin c | Vitamin c (as ascorbic acid) | E-300 | FEMA NO. 2109 | INS NO.300 | INS-300 | NSC-218455 | NSC-33832

Trade Names(13): Ascor | Ascur | Bassett's | Cecon | Cenolate | Haliborange | Redoxon | Redoxon c | Redoxon chew-c | Redoxon slow release | Top c | Vital life | Vitamin C

Canonical SMILES:  O=C1O[C@H]([C@@H](O)CO)C(O)=C1O

Standard InChI:  InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1

Standard InChI Key:  CIWBSHSKHKDKBQ-JLAZNSOCSA-N

Alternative Forms

1. Parent:

   

   ALA196

   ASCORBIC ACID

2. Alternative Forms:

   

   ALA196

   ---

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 176.12

Molecular Weight (Monoisotopic): 176.0321

AlogP: -1.41

#Rotatable Bonds: 2

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.36

CX Basic pKa: ┄

CX LogP: -1.91

CX LogD: -4.83

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.39

Np Likeness Score: 2.26

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175. Cuong TD, Hung TM, Kim JC, Kim EH, Woo MH, Choi JS, Lee JH, Min BS..  (2012)  Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.,  75  (12): [PMID:23234407] [10.1021/np3003673]

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183. Mallesha L, Mohana KN, Veeresh B.  (2012)  Synthesis and biological activities of Schiff bases of gabapentin with different aldehydes and ketones: a structureactivity relationship study,  21  (1): [10.1007/s00044-010-9498-8]

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186. Dinakaran VS, Jacob D, Mathew JE.  (2012)  Synthesis and biological evaluation of novel pyrimidine-2(1H)-ones/thiones as potent anti-inflammatory and anticancer agents,  21  (11): [10.1007/s00044-011-9909-5]

187. Bandgar BP, Hote BS, Jalde SS, Gacche RN.  (2012)  Synthesis and biological evaluation of novel curcumin analogues as anti-inflammatory, anti-cancer and anti-oxidant agents,  21  (10): [10.1007/s00044-011-9834-7]

188. Milian L, Ballesteros R, Sanz MJ, Blazquez MA.  (2012)  Synthesis and reactive oxygen species scavenging activity of halogenated alkaloids from boldine,  21  (10): [10.1007/s00044-011-9844-5]

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191. Gouda MA, Berghot MA, Baz EA, Hamama WS.  (2012)  Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety,  21  (7): [10.1007/s00044-011-9610-8]

192. Karki SS, Bhutle SR, Pedgaonkar GS, Zubaidha PK, Shaikh RM, Rajput CG, Shendarkar GS.  (2011)  Synthesis and biological evaluation of some stilbene-based analogues,  20  (8): [10.1007/s00044-010-9450-y]

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194. Bayoumi WA, Elsayed MA.  (2012)  Synthesis of new phenylcarbamoylbenzoic acid derivatives and evaluation of their in vitro antioxidant activity,  21  (8): [10.1007/s00044-011-9677-2]

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198. Rajguru D, Keshwal BS, Jain S.  (2013)  Solvent-free, green and efficient synthesis of pyrano[4, 3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents,  22  (12): [10.1007/s00044-013-0586-4]

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201. Sheikh J, Hadda TB.  (2013)  Antibacterial, antifungal and antioxidant activity of some new water-soluble -diketones,  22  (2): [10.1007/s00044-012-0089-8]

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204. Tian SZ, Pu X, Luo G, Zhao LX, Xu LH, Li WJ, Luo Y..  (2013)  Isolation and characterization of new p-Terphenyls with antifungal, antibacterial, and antioxidant activities from halophilic actinomycete Nocardiopsis gilva YIM 90087.,  61  (12): [PMID:23441911] [10.1021/jf400718w]

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206. Prashanth MK, Revanasiddappa HD.  (2013)  Synthesis of some new glutamine linked 2,3-disubstituted quinazolinone derivatives as potent antimicrobial and antioxidant agents,  22  (6): [10.1007/s00044-012-0269-6]

207. Narsinghani T, Sharma MC, Bhargav S.  (2013)  Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives,  22  (9): [10.1007/s00044-012-0413-3]

208. Parveen M, Ali A, Alam M, Khan AU, Ahmad A.  (2013)  Synthesis, characterization, biological evaluation and in silico screening of oxadiazinanones,  22  (7): [10.1007/s00044-012-0313-6]

209. Rajasekaran A, Devi KS.  (2013)  Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl)urea derivatives,  22  (6): [10.1007/s00044-012-0255-z]

210. Zhang Y, Fang Y, Liang H, Wang H, Hu K, Liu X, Yi X, Peng Y..  (2013)  Synthesis and antioxidant activities of 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives.,  23  (1): [PMID:23206864] [10.1016/j.bmcl.2012.11.006]

211. Yoon H, Kim TW, Shin SY, Park MJ, Yong Y, Kim DW, Islam T, Lee YH, Jung KY, Lim Y..  (2013)  Design, synthesis and inhibitory activities of naringenin derivatives on human colon cancer cells.,  23  (1): [PMID:23177257] [10.1016/j.bmcl.2012.10.130]

212. Mandawad GG, Dawane BS, Beedkar SD, Khobragade CN, Yemul OS..  (2013)  Trisubstituted thiophene analogues of 1-thiazolyl-2-pyrazoline, super oxidase inhibitors and free radical scavengers.,  21  (1): [PMID:23177727] [10.1016/j.bmc.2012.09.060]

213. Cervellati R, Galletti P, Greco E, Cocuzza CE, Musumeci R, Bardini L, Paolucci F, Pori M, Soldati R, Giacomini D..  (2013)  Monocyclic β-lactams as antibacterial agents: facing antioxidant activity of N-methylthio-azetidinones.,  60  [PMID:23314047] [10.1016/j.ejmech.2012.12.024]

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215. Bidon-Chanal A, Fuertes A, Alonso D, Pérez DI, Martínez A, Luque FJ, Medina M..  (2013)  Evidence for a new binding mode to GSK-3: allosteric regulation by the marine compound palinurin.,  60  [PMID:23354070] [10.1016/j.ejmech.2012.12.014]

216. Beena, Kumar D, Rawat DS..  (2013)  Synthesis and antioxidant activity of thymol and carvacrol based Schiff bases.,  23  (3): [PMID:23273412] [10.1016/j.bmcl.2012.12.001]

217. Josey BJ, Inks ES, Wen X, Chou CJ..  (2013)  Structure-activity relationship study of vitamin k derivatives yields highly potent neuroprotective agents.,  56  (3): [PMID:23327468] [10.1021/jm301485d]

218. Shenvi S, Kumar K, Hatti KS, Rijesh K, Diwakar L, Reddy GC..  (2013)  Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: structure-activity relationship.,  62  [PMID:23395966] [10.1016/j.ejmech.2013.01.018]

219. Tronina T, Bartmańska A, Filip-Psurska B, Wietrzyk J, Popłoński J, Huszcza E..  (2013)  Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.,  21  (7): [PMID:23434138] [10.1016/j.bmc.2013.01.026]

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221. Koparir M, Orek C, Parlak AE, Söylemez A, Koparir P, Karatepe M, Dastan SD..  (2013)  Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones.,  63  [PMID:23517726] [10.1016/j.ejmech.2013.02.025]

222. Razavi SF, Khoobi M, Nadri H, Sakhteman A, Moradi A, Emami S, Foroumadi A, Shafiee A..  (2013)  Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors.,  64  [PMID:23644208] [10.1016/j.ejmech.2013.03.021]

223. Marković V, Janićijević A, Stanojković T, Kolundžija B, Sladić D, Vujčić M, Janović B, Joksović L, Djurdjević PT, Todorović N, Trifunović S, Joksović MD..  (2013)  Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group.,  64  [PMID:23644206] [10.1016/j.ejmech.2013.03.071]

224. Hoobler EK, Holz C, Holman TR..  (2013)  Pseudoperoxidase investigations of hydroperoxides and inhibitors with human lipoxygenases.,  21  (13): [PMID:23669189] [10.1016/j.bmc.2013.04.016]

225. Ningaiah S, Bhadraiah UK, Keshavamurthy S, Javarasetty C..  (2013)  Novel pyrazoline amidoxime and their 1,2,4-oxadiazole analogues: synthesis and pharmacological screening.,  23  (16): [PMID:23850201] [10.1016/j.bmcl.2013.06.042]

226. El-Borai MA, Rizk HF, Beltagy DM, El-Deeb IY..  (2013)  Microwave-assisted synthesis of some new pyrazolopyridines and their antioxidant, antitumor and antimicrobial activities.,  66  [PMID:23831694] [10.1016/j.ejmech.2013.04.043]

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228. Alarif WM, Abdel-Lateff A, Al-Abd AM, Basaif SA, Badria FA, Shams M, Ayyad SE..  (2013)  Selective cytotoxic effects on human breast carcinoma of new methoxylated flavonoids from Euryops arabicus grown in Saudi Arabia.,  66  [PMID:23800391] [10.1016/j.ejmech.2013.05.025]

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232. Kanekar Y, Basha K, Duche S, Gupte R, Kapat A..  (2013)  Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.,  67  [PMID:23933533] [10.1016/j.ejmech.2013.06.016]

233. Mishra OP, Simmons N, Tyagi S, Pietrofesa R, Shuvaev VV, Valiulin RA, Heretsch P, Nicolaou KC, Christofidou-Solomidou M..  (2013)  Synthesis and antioxidant evaluation of (S,S)- and (R,R)-secoisolariciresinol diglucosides (SDGs).,  23  (19): [PMID:23978651] [10.1016/j.bmcl.2013.07.062]

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236. Mohamed MS, Youns MM, Ahmed NM..  (2013)  Synthesis, antimicrobial, antioxidant activities of novel 6-aryl-5-cyano thiouracil derivatives.,  69  [PMID:24095752] [10.1016/j.ejmech.2013.08.032]

237. Unpublished dataset, 

238. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

239. Patil VP, Markad VL, Kodam KM, Waghmode SB..  (2013)  Facile preparation of tetrahydro-5H-pyrido[1,2,3-de]-1,4-benzoxazines via reductive cyclization of 2-(8-quinolinyloxy)ethanones and their antioxidant activity.,  23  (23): [PMID:24157368] [10.1016/j.bmcl.2013.09.088]

240. Yang S, Li X, Hu F, Li Y, Yang Y, Yan J, Kuang C, Yang Q..  (2013)  Discovery of tryptanthrin derivatives as potent inhibitors of indoleamine 2,3-dioxygenase with therapeutic activity in Lewis lung cancer (LLC) tumor-bearing mice.,  56  (21): [PMID:24099220] [10.1021/jm401195n]

241. Weon JB, Ko HJ, Ma CJ..  (2013)  The ameliorating effects of 2,3-dihydroxy-4-methoxyacetophenone on scopolamine-induced memory impairment in mice and its neuroprotective activity.,  23  (24): [PMID:24210692] [10.1016/j.bmcl.2013.10.032]

242. Hanke T, Dehm F, Liening S, Popella SD, Maczewsky J, Pillong M, Kunze J, Weinigel C, Barz D, Kaiser A, Wurglics M, Lämmerhofer M, Schneider G, Sautebin L, Schubert-Zsilavecz M, Werz O..  (2013)  Aminothiazole-featured pirinixic acid derivatives as dual 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 inhibitors with improved potency and efficiency in vivo.,  56  (22): [PMID:24171493] [10.1021/jm401557w]

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244. Yan SL, Su YF, Chen L, Que M, Gao XM, Chang JB..  (2014)  Polygonumosides A-D, stilbene derivatives from processed roots of Polygonum multiflorum.,  77  (2): [PMID:24499304] [10.1021/np400720y]

245. Benz S, Nötzli S, Siegel JS, Eberli D, Jessen HJ..  (2013)  Controlled oxygen release from pyridone endoperoxides promotes cell survival under anoxic conditions.,  56  (24): [PMID:24299550] [10.1021/jm4016137]

246. Domínguez-Álvarez E, Plano D, Font M, Calvo A, Prior C, Jacob C, Palop JA, Sanmartín C..  (2014)  Synthesis and antiproliferative activity of novel selenoester derivatives.,  73  [PMID:24389510] [10.1016/j.ejmech.2013.11.034]

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248. Kotaiah Y, Nagaraju K, Harikrishna N, Venkata Rao C, Yamini L, Vijjulatha M..  (2014)  Synthesis, docking and evaluation of antioxidant and antimicrobial activities of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidines.,  75  [PMID:24531232] [10.1016/j.ejmech.2014.01.006]

249. PubChem BioAssay data set, 

250. PubChem BioAssay data set, 

251. PubChem BioAssay data set, 

252. PubChem BioAssay data set, 

253. Haseena banu B, Prasad KV, Bharathi K..  (2014)  Synthesis and biological evaluation of N-dehydrodipeptidyl-N,N'-dicyclohexylurea analogs.,  78  [PMID:24681067] [10.1016/j.ejmech.2014.03.037]

254. Ma K, Han J, Bao L, Wei T, Liu H..  (2014)  Two sarcoviolins with antioxidative and α-glucosidase inhibitory activity from the edible mushroom Sarcodon leucopus collected in Tibet.,  77  (4): [PMID:24645629] [10.1021/np401026b]

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257. Sivakumar KK, Rajasekaran A, Senthilkumar P, Wattamwar PP..  (2014)  Conventional and microwave assisted synthesis of pyrazolone Mannich bases possessing anti-inflammatory, analgesic, ulcerogenic effect and antimicrobial properties.,  24  (13): [PMID:24835630] [10.1016/j.bmcl.2014.04.067]

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259. Koeberle A, Muñoz E, Appendino GB, Minassi A, Pace S, Rossi A, Weinigel C, Barz D, Sautebin L, Caprioglio D, Collado JA, Werz O..  (2014)  SAR studies on curcumin's pro-inflammatory targets: discovery of prenylated pyrazolocurcuminoids as potent and selective novel inhibitors of 5-lipoxygenase.,  57  (13): [PMID:24920381] [10.1021/jm500308c]

260. Yu HY, Chen ZY, Sun B, Liu J, Meng FY, Liu Y, Tian T, Jin A, Ruan HL..  (2014)  Lignans from the fruit of Schisandra glaucescens with antioxidant and neuroprotective properties.,  77  (6): [PMID:24927000] [10.1021/np4010536]

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262. Barakat A, Al-Majid AM, Al-Najjar HJ, Mabkhot YN, Javaid S, Yousuf S, Choudhary MI..  (2014)  Zwitterionic pyrimidinium adducts as antioxidants with therapeutic potential as nitric oxide scavenger.,  84  [PMID:25016372] [10.1016/j.ejmech.2014.07.026]

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351. Bautista E, Ortiz-Pastrana N, Pastor-Palacios G, Montoya-Contreras A, Toscano RA, Morales-Jiménez J, Salazar-Olivo LA, Ortega A..  (2017)  neo-Clerodane Diterpenoids from Salvia polystachya Stimulate the Expression of Extracellular Matrix Components in Human Dermal Fibroblasts.,  80  (11): [PMID:29135252] [10.1021/acs.jnatprod.7b00591]

352. Zhu Y, Pan WH, Ku CF, Zhang HJ, Tsang SW..  (2018)  Design, synthesis and evaluation of novel dihydrostilbene derivatives as potential anti-melanogenic skin-protecting agents.,  143  [PMID:29150333] [10.1016/j.ejmech.2017.10.014]

353. ElBordiny HS, El-Miligy MM, Kassab SE, Daabees H, Mohamed Ali WA, Abdelhamid Mohamed El-Hawash S..  (2018)  Design, synthesis, biological evaluation and docking studies of new 3-(4,5-dihydro-1H-pyrazol/isoxazol-5-yl)-2-phenyl-1H-indole derivatives as potent antioxidants and 15-lipoxygenase inhibitors.,  145  [PMID:29339254] [10.1016/j.ejmech.2018.01.026]

354. Jalili-Baleh L, Forootanfar H, Küçükkılınç TT, Nadri H, Abdolahi Z, Ameri A, Jafari M, Ayazgok B, Baeeri M, Rahimifard M, Abbas Bukhari SN, Abdollahi M, Ganjali MR, Emami S, Khoobi M, Foroumadi A..  (2018)  Design, synthesis and evaluation of novel multi-target-directed ligands for treatment of Alzheimer's disease based on coumarin and lipoic acid scaffolds.,  152  [PMID:29763808] [10.1016/j.ejmech.2018.04.058]

355. Ayati A, Oghabi Bakhshaiesh T, Moghimi S, Esmaeili R, Majidzadeh-A K, Safavi M, Firoozpour L, Emami S, Foroumadi A..  (2018)  Synthesis and biological evaluation of new coumarins bearing 2,4-diaminothiazole-5-carbonyl moiety.,  155  [PMID:29908441] [10.1016/j.ejmech.2018.06.015]

356. Martínez A, Zahran M, Gomez M, Cooper C, Guevara J, Ekengard E, Nordlander E, Alcendor R, Hambleton S..  (2018)  Novel multi-target compounds in the quest for new chemotherapies against Alzheimer's disease: An experimental and theoretical study.,  26  (17): [PMID:30181028] [10.1016/j.bmc.2018.08.019]

357. Abbhi V, Saini L, Mishra S, Sethi G, Kumar AP, Piplani P..  (2017)  Design and synthesis of benzimidazole-based Rho kinase inhibitors for the treatment of glaucoma.,  25  (21): [PMID:29033348] [10.1016/j.bmc.2017.09.045]

358. Singh M, Kaur M, Singh N, Silakari O..  (2017)  Exploration of multi-target potential of chromen-4-one based compounds in Alzheimer's disease: Design, synthesis and biological evaluations.,  25  (24): [PMID:29089261] [10.1016/j.bmc.2017.09.012]

359. Bae D, Gautam J, Jang H, Banskota S, Lee SY, Jeong MJ, Kim AS, Kim HC, Lee IH, Nam TG, Kim JA, Jeong BS..  (2018)  Protective effects of 6-ureido/thioureido-2,4,5-trimethylpyridin-3-ols against 4-hydroxynonenal-induced cell death in adult retinal pigment epithelial-19 cells.,  28  (2): [PMID:29208521] [10.1016/j.bmcl.2017.11.046]

360. Pagire SH, Lee E, Pagire HS, Bae EJ, Ryu SJ, Lee D, Kim MH, Kim GR, Hwang KS, Ahn S, Maeng JH, Song JS, Bae MA, Lee DH, Ahn JH..  (2018)  Design, synthesis and biological evaluation of glutamic acid derivatives as anti-oxidant and anti-inflammatory agents.,  28  (3): [PMID:29295794] [10.1016/j.bmcl.2017.11.012]

361. Patil SR, Bollikonda S, Patil RH, Sangshetti JN, Bobade AS, Asrondkar A, Reddy PP, Shinde DB..  (2018)  Microwave-assisted synthesis of novel 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones as antileishmanial and antioxidant agents.,  28  (3): [PMID:29258770] [10.1016/j.bmcl.2017.12.013]

362. Moraux T, Dumarçay S, Gérardin P, Gérardin-Charbonnier C..  (2017)  Derivatives of the Lignan 7'-Hydroxymatairesinol with Antioxidant Properties and Enhanced Lipophilicity.,  80  (6): [PMID:28590734] [10.1021/acs.jnatprod.6b01124]

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364. Kumar D, Gupta SK, Ganeshpurkar A, Gutti G, Krishnamurthy S, Modi G, Singh SK..  (2018)  Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease.,  150  [PMID:29524731] [10.1016/j.ejmech.2018.02.078]

365. Sathiyachandran P, Manogaran P, Nesterov VN, Padma VV, Rajendra Prasad KJ..  (2018)  Design and synthesis of novel pyrrolo[2,3-a]carbazoles: 7-Chloro-2-oxo-3a-(2'-oxo-2',3'-dihydro-1'H-indol-3'-yl)-2,3,3a,4,5,10-hexahydro-pyrrolo[3,2-a]carbazole-1-carbonitrile as an efficient anticancer agent.,  150  [PMID:29597168] [10.1016/j.ejmech.2018.03.056]

366. Pang X, Lin X, Yang J, Zhou X, Yang B, Wang J, Liu Y..  (2018)  Spiro-Phthalides and Isocoumarins Isolated from the Marine-Sponge-Derived Fungus Setosphaeria sp. SCSIO41009.,  81  (8): [PMID:30091601] [10.1021/acs.jnatprod.8b00345]

367. Gurjar AS, Darekar MN, Yeong KY, Ooi L..  (2018)  In silico studies, synthesis and pharmacological evaluation to explore multi-targeted approach for imidazole analogues as potential cholinesterase inhibitors with neuroprotective role for Alzheimer's disease.,  26  (8): [PMID:29429576] [10.1016/j.bmc.2018.01.029]

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373. Pavelyev RS, Bondar OV, Nguyen TNT, Ziganshina AA, Al Farroukh M, Karwt R, Alekbaeva GD, Pugachev MV, Yamaleeva ZR, Kataeva ON, Balakin KV, Shtyrlin YG..  (2018)  Synthesis and in vitro antitumor activity of novel alkenyl derivatives of pyridoxine, bioisosteric analogs of feruloyl methane.,  26  (22): [PMID:30429098] [10.1016/j.bmc.2018.10.031]

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376. Unpublished dataset, 

377. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

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383. Srivastava P, Tripathi PN, Sharma P, Rai SN, Singh SP, Srivastava RK, Shankar S, Shrivastava SK..  (2019)  Design and development of some phenyl benzoxazole derivatives as a potent acetylcholinesterase inhibitor with antioxidant property to enhance learning and memory.,  163  [PMID:30503937] [10.1016/j.ejmech.2018.11.049]

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387. Wu M, Ma J, Ji L, Wang M, Han J, Li Z..  (2019)  Design, synthesis, and biological evaluation of rutacecarpine derivatives as multitarget-directed ligands for the treatment of Alzheimer's disease.,  177  [PMID:31136894] [10.1016/j.ejmech.2019.05.055]

388. Shaaban S, Ashmawy AM, Negm A, Wessjohann LA..  (2019)  Synthesis and biochemical studies of novel organic selenides with increased selectivity for hepatocellular carcinoma and breast adenocarcinoma.,  179  [PMID:31276896] [10.1016/j.ejmech.2019.06.075]

389. Cocolas AH, Parks EL, Ressler AJ, Havasi MH, Seeram NP, Henry GE..  (2019)  Heterocyclic β-keto sulfide derivatives of carvacrol: Synthesis and copper (II) ion reducing capacity.,  29  (19): [PMID:31474483] [10.1016/j.bmcl.2019.126636]

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394. Bindu B, Vijayalakshmi S, Manikandan A..  (2020)  Synthesis and discovery of triazolo-pyridazine-6-yl-substituted piperazines as effective anti-diabetic drugs; evaluated over dipeptidyl peptidase-4 inhibition mechanism and insulinotropic activities.,  187  [PMID:31812034] [10.1016/j.ejmech.2019.111912]

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396. Lee S, Ullah S, Park C, Won Lee H, Kang D, Yang J, Akter J, Park Y, Chun P, Moon HR..  (2019)  Inhibitory effects of N-(acryloyl)benzamide derivatives on tyrosinase and melanogenesis.,  27  (17): [PMID:31345746] [10.1016/j.bmc.2019.07.034]

397. Luo HY, Guo RX, Yu XK, Zhang X, Lu YQ, Wu HW, Tang LY, Wang ZJ..  (2019)  Chemical constituents from the seeds of Cassia obtusefolia and their in vitro α-glucosidase inhibitory and antioxidant activities.,  29  (13): [PMID:31078411] [10.1016/j.bmcl.2019.05.002]

398. Sudhapriya N, Manikandan A, Kumar MR, Perumal PT..  (2019)  Cu-mediated synthesis of differentially substituted diazepines as AChE inhibitors; validation through molecular docking and Lipinski's filter to develop novel anti-neurodegenerative drugs.,  29  (11): [PMID:30956014] [10.1016/j.bmcl.2019.04.002]

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400. Husain A, Khan SA, Iram F, Iqbal MA, Asif M..  (2019)  Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.,  171  [PMID:30909021] [10.1016/j.ejmech.2019.03.021]

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402. Wang D, Zhu J, Xu JR, Ji DD..  (2019)  Synthesis of N-hydroxycinnamoyl amide derivatives and evaluation of their anti-oxidative and anti-tyrosinase activities.,  27  (20): [PMID:31178269] [10.1016/j.bmc.2019.05.031]

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405. Rosada B, Bekier A, Cytarska J, Płaziński W, Zavyalova O, Sikora A, Dzitko K, Łączkowski KZ..  (2019)  Benzo[b]thiophene-thiazoles as potent anti-Toxoplasma gondii agents: Design, synthesis, tyrosinase/tyrosine hydroxylase inhibitors, molecular docking study, and antioxidant activity.,  184  [PMID:31629163] [10.1016/j.ejmech.2019.111765]

406. Khudina OG, Makhaeva GF, Elkina NA, Boltneva NP, Serebryakova OG, Shchegolkov EV, Rudakova EV, Lushchekina SV, Burgart YV, Bachurin SO, Richardson RJ, Saloutin VI..  (2019)  Synthesis of 2-arylhydrazinylidene-3-oxo-4,4,4-trifluorobutanoic acids as new selective carboxylesterase inhibitors and radical scavengers.,  29  (23): [PMID:31640885] [10.1016/j.bmcl.2019.126716]

407. Reis JS, Corrêa MA, Ribeiro CA, Dos Santos JL..  (2019)  Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer.,  29  (24): [PMID:31732408] [10.1016/j.bmcl.2019.126755]

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417. Yang ZN, Su BJ, Wang YQ, Liao HB, Chen ZF, Liang D..  (2020)  Isolation, Absolute Configuration, and Biological Activities of Chebulic Acid and Brevifolincarboxylic Acid Derivatives from Euphorbia hirta.,  83  (4): [PMID:32141299] [10.1021/acs.jnatprod.9b00877]

418. Zampieri D, Fortuna S, Calabretti A, Romano M, Menegazzi R, Schepmann D, Wünsch B, Mamolo MG..  (2020)  Synthesis, Cytotoxicity Evaluation, and Computational Insights of Novel 1,4-Diazepane-Based Sigma Ligands.,  11  (5): [PMID:32435366] [10.1021/acsmedchemlett.9b00524]

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420. Xie YD, Liu JP, Wang W, Shi YH, Wang XP, Sun M, Xu XY, Li N..  (2020)  3,4-Dihydroxyphenethyl nitrate with nitric oxide releasing, antioxidant, hypoglycemic and hypolipidemic effects.,  30  (15): [PMID:32527456] [10.1016/j.bmcl.2020.127277]

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Source

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• Clinical Candidates
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• DrugMatrix
• Gene Expression Atlas Compounds
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• RESOLUTE - Research Empowerment on Solute Carriers