- Asymmetric synthesis of (+)-indatraline using rhodium-catalyzed C-H activation
-
The potent monoamine reuptake inhibitor (+)-indatraline, 1, was prepared in greater than 98% ee employing a highly enantioselective carbenoid C-H insertion reaction into 1,4-cyclohexadiene catalyzed by the chiral rhodium complex, Rh2(S-DOSP)4.
- Davies, Huw M.L.,Gregg, Timothy M.
-
-
Read Online
- Sertraline derivative and preparation method and application thereof
-
The invention discloses a sertraline derivative or a medicinal salt thereof. The structural general formula of the sertraline derivative is shown in the specification. The sertraline derivative has a good inhibition effect on cryptococcus neoformans, particularly, the compound D16 disclosed by the invention has a relatively good inhibition effect on candida glabrata 9073, candida tropicalis 10186, cryptococcus neoformans, candida albicans 5314, candida albicans 904, candida tropicalis 10186, drug-resistant candida albicans 103 and cryptococcus gottii.
- -
-
Paragraph 0084-0086; 0089-0090
(2021/04/14)
-
- Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: Applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine
-
Efficient kinetic resolution (KR) occurs in asymmetric transfer hydrogenation (ATH) reactions of racemic 3-aryl-1-indanones using commercial (R,R)- or (S,S)-Ts-DENEB as a catalyst, a 1?:?5 mixture of HCO2H and Et3N as a hydrogen source and MeOH as solvent
- Lee, Hyeon-Kyu,Park, Songsoon
-
p. 23161 - 23183
(2021/07/24)
-
- Metal free decarboxylative aminoxylation of carboxylic acids using a biphasic solvent system
-
The smooth oxidative radical decarboxylation of carboxylic acids with TEMPO and other derivatives as radical scavengers is reported. The key to success was the use of a two-phase solvent system to avoid otherwise predominant side reactions such as the oxidation of TEMPO by persulfate and enabled the selective formation of synthetically useful alkoxyamines. The method does not require transition metals and was successfully used in a new synthetic approach for the antidepressant indatraline.
- Schulz, G?ran,Kirschning, Andreas
-
supporting information
p. 273 - 278
(2021/01/14)
-
- Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5- Endo-Trig Cyclization
-
A nickel-catalyzed reductive cyclization of enones affords a wide array of indanones in high enantiomeric induction. The reaction is featured with an unprecedented broad scope of substrates. The versatility of the new method is demonstrated in several short stereoselective syntheses of medically valuable (R)-tolterodine, parent and deuterated (+)-indatraline, and an antitumor natural product, (+)-multisianthol. In comparison, these compounds cannot be prepared satisfactorily via analogous processes catalyzed by palladium.
- Qin, Xurong,Yao Lee, Marcus Wen,Zhou, Jianrong Steve
-
p. 5990 - 5994
(2019/08/20)
-
- Asymmetric total synthesis of (+)-indatraline via diastereoselective amination of chiral ethers using chlorosulfonyl isocyanate
-
A concise asymmetric total synthesis of (+)-indatraline from readily available cinnamic acid is described. The key steps include Corey's oxazaborolidine-catalyzed asymmetric carbonyl reduction and a highly stereoselective amination of chiral benzylic ether with retention of stereochemistry using chlorosulfonyl isocyanate.
- Lee, Sang Hwi,Park, Sook Jin,Kim, In Su,Jung, Young Hoon
-
p. 1877 - 1880
(2013/03/13)
-
- Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology
-
The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H2O), or a solvent switch to CHCl3, to achieve high yields and high selectivities.
- Roesner, Stefan,Casatejada, Javier Mansilla,Elford, Tim G.,Sonawane, Ravindra P.,Aggarwal, Varinder K.
-
p. 5740 - 5743
(2011/12/22)
-
- Synthesis of optically pure 1-amino-3-aryl indanes exemplified by (+)-indatraline
-
A versatile procedure for the synthesis of optically pure 1-amino-3-aryl indanes is presented, exemplified by the synthesis of the triple uptake inhibitor (+)-indatraline (1). Georg Thieme Verlag Stuttgart · New York.
- N?rager, Niels Gr?n,Lorentz-Petersen, Linda Luise Reeh,Lyngs?, Lars Ole,Kehler, Jan,Juhl, Karsten
-
p. 1753 - 1755
(2011/09/16)
-
- Synthesis and Evaluation of Indatraline-Based Inhibitors for Trypanothione Reductase
-
The search for novel compounds of relevance to the treatment of diseases caused by trypanosomatid protozoan parasites continues. Screening of a large library of known bioactive compounds has led to several drug-like starting points for further optimisation. In this study, novel analogues of the monoamine uptake inhibitor indatraline were prepared and assessed both as inhibitors of trypanothione reductase (TryR) and against the parasite Trypanosoma brucei. Although it proved difficult to significantly increase the potency of the original compound as an inhibitor of TryR, some insight into the preferred substituent on the amine group and in the two aromatic rings of the parent indatraline was deduced. In addition, detailed mode of action studies indicated that two of the inhibitors exhibit a mixed mode of inhibition. Give these inhibitors a TryR: Indatraline is a CNS-active inhibitor of trypanothione reductase (TryR) revealed in a previous high-throughput screen. For this study we prepared analogues of indatraline and tested their capacity to inhibit TryR and the proliferation of Trypanosoma brucei cells. Inhibitors of micromolar potency with a mixed mode of inhibition were identified.
- Walton, Jeffrey G. A.,Jones, Deuan C.,Kiuru, Paula,Durie, Alastair J.,Westwood, Nicholas J.,Fairlamb, Alan H.
-
p. 321 - 328
(2012/01/12)
-
- TREATMENT OF NEURODEGENERATIVE DISEASES USING INDATRALINE ANALOGS
-
Methods and compositions useful in the treatment or prevention of synucleinopathies, such as Parkinson''s disease, diffuse Lewy body disease, and multiple system atrophy, or other neurodegenerative diseases (e.g., amyotrophic lateral sclerosis, Huntington''s disease, and Alzheimer''s disease) are provided. The treatment including administering to a subject an indatraline derivative that inhibits the aggregation of a-synuclein.
- -
-
-
- Synthesis of indatraline using a Suzuki cross-coupling reaction and a chemoselective hydrogenation: A versatile approach
-
Indatraline and its derivatives can be obtained in five steps from indanone by using a Suzuki cross-coupling reaction and a chemoselective hydrogenation catalyzed by Wilkinson's catalyst.
- Cossy, Janine,Belotti, Damien,Maguer, Aude
-
p. 1515 - 1517
(2007/10/03)
-
- 3-Phenyl-1-indanamines. Potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake
-
A series of 3-phenyl-1-indanamines was synthesized and tested for potential antidepressant activity and for inhibition of dopamine (DA), norepinephrine (NE), and serotonin (5-HT) uptake. Transisomers were generally potent inhibitors of DA, NE, and 5-HT up
- Bogeso,Christensen,Hyttel,Liljefors
-
p. 1817 - 1828
(2007/10/02)
-