175463-32-8

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1-Boc-3-cyano-4-oxopyrrolidine is used as a key intermediate in the synthesis of new napthyridone antibacterials. These antibacterials are essential for developing novel treatments against resistant bacterial strains, contributing to the fight against antibiotic resistance.
2. Used in the Synthesis of Gemifloxacin Derivatives:
1-Boc-3-cyano-4-oxopyrrolidine is also utilized in the synthesis of gemifloxacin derivatives containing a benzyloxime moiety. Gemifloxacin is a fluoroquinolone antibiotic used to treat various bacterial infections. The development of novel gemifloxacin derivatives with improved properties, such as enhanced efficacy or reduced side effects, is crucial for addressing the challenges posed by antibiotic resistance.
3. Used in the Chemical Industry:
In the chemical industry, 1-Boc-3-cyano-4-oxopyrrolidine can be employed as a building block for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable asset in the development of new molecules with potential applications in various fields.

InChI:InChI=1/C10H14N2O3/c1-10(2,3)15-9(14)12-5-7(4-11)8(13)6-12/h7H,5-6H2,1-3H3

Upstream product

• 266353-18-8 N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester 
• 44981-94-4 N-cyanoethyl glycine ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 44915-39-1 [(2-cyanoethyl)amino]acetic acid methyl ester 
• 3088-42-4 N-(2-cyanoethyl)glycine 
• 266353-19-9 [tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester 

Downstream Products

• 197143-33-2 tert-butyl 3-cyano-4-hydroxypyrrolidine-1-carboxylate 
• 398491-59-3 3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 773826-73-6 tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate 
• 175463-34-0 4-(tert-butoxycarbonyl)aminomethyl-1-(t-butoxycarbonyl)pyrrolidin-3-ol 
• 175463-14-6 gemifloxacin 
• 398491-59-3 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 1227461-24-6 4-cyano-3-amino-1-(N-tert-butoxycarbonyl)-3,4-pyrroline 
• 175463-36-2 tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate 
• 1280210-79-8 2,6-dihydropyrrole [3,4-c]pyrazole-5(4H)-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis and in-vitro antibacterial activity of 7-(3-aminopyrrolo[3,4-c] pyrazol-5(2H,4H,6H)-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives

A series of novel 7-(3-aminopyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)-6-fluoro- 4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives was designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in-vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Generally, all of the target compounds display rather weak potency against the tested Gram-negative strains, but most of them exhibit good potency in inhibiting the growth of S. aureus including methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis including methicillin-resistant S. epidermidis (MRSE) (MIC: 0.125-8 μg/mL). In particular, the compound 9g is 2 to 32 fold more potent than gemifloxacin (GM), moxifloxacin (MX), gatifloxacin (GT), and levofloxacin (LV) against S. pneumoniae 08-3, K. pneumoniae 09-23, and P. aeruginosa ATCC27853, 4 to 32 fold more potent than MX, GM, and LV against K. pneumoniae 09-21, and more active than or comparable to the four reference drugs against P. aeruginosa 09-32. A series of novel fluoroquinolone derivatives was designed and synthesized. All target compounds display rather weak potency against the tested Gram-negative strains, but most of them exhibit good potency in inhibiting the growth of Staphylococcus aureus and Staphylococcus epidermidis. In particular, the compound 9g is the most promising drug.

Discovery of gemifloxacin (Factive, LB20304a): A quinolone of new a generation

Novel quinolone antibacterials, which bear an alkyloxime substituent in the 4-position and an aminomethyl substituent in the 3-position of the pyrrolidine ring, have been designed and synthesized. These fluoroquinolones were found to possess extremely potent antimicrobial activity against Gram-positive organisms including resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Among these compounds our development candidate, Gemifloxacin (Factive, LB20304a), showed the best in vivo efficacy and pharmacokinetic profile in animals, as well as good safety pharmacological properties. Gemifloxacin was found to be especially effective against respiratory tract infections that account for over 70% of all infections. With once-a-day dosage, potency against respiratory tract infections such as chronic bronchitis and pneumonia was ensured without any significant side effect. In December 1999, Gemifloxacin filed a NDA for marketing approval to the US Food and Drug Administration. Copyright

A preparation method of the lucky mischa star side chain

The invention relates to a preparation method of a gemifloxacin side chain. The preparation method comprises that N-tertbutyloxycarbonyl-4-cyano-3-pyrrolidone is prepared or taken and then reacts with trimethyl orthoformate to produce N-tertbutyloxycarbonyl-4-cyano-3-dimethoxypyrrolidone, the N-tertbutyloxycarbonyl-4-cyano-3-dimethoxypyrrolidone, methanol, a catalyst and (BOC)2 anhydride undergo a complete reaction at a room temperature to produce N-tertbutyloxycarbonyl-4-aminomethyl-3-dimethoxypyrrolidone, the N-tertbutyloxycarbonyl-4-aminomethyl-3-dimethoxypyrrolidone and HAC undergo a complete reaction at a room temperature with stirring to produce N-tertbutyloxycarbonyl-4-aminomethyl-3-pyrrolidone, and the N-tertbutyloxycarbonyl-4-aminomethyl-3-pyrrolidone is transformed into the gemifloxacin side chain 4-aminomethyl-3-methoxyiminopyrrolidone. The preparation method has simple processes, allows mild reaction conditions easily to be realized, has a low raw material price, a low cost and less environmental pollution and creates a novel gemifloxacin side chain pyrrolidone ketonic group protection method and a gemifloxacin side chain synthesis route.

Preparation method of zabofloxacin intermediate

The invention provides a preparation method of a zabofloxacin intermediate. The method comprises: reacting ethyl glycinate hydrochloride with acrylonitrile under catalysis of a base to form an intermediate I; then reacting the intermediate I with Boc anhydride under the function of a strong base to generate an intermediate III; reacting the intermediate III, the methoxyamine hydrochloride and formaldehyde to generate an intermediate IV; and then preparing the zabofloxacin intermediate by reacting the intermediate IV with methanesulfonyl chloride, performing reduction with sodium borohydride, and other steps. The zabofloxacin intermediate is prepared through nine steps with a high yield and high quality by the method, the material adding amount reaches the level of hundreds of grams, and the method is suitable for industrial production.

(R)- N - [5 - (2 - methoxy - 2 - phenyl-acetyl) - 1, 4, 5, 6 - tetrahydro-pyrrolo [3, 4 - c] pyrazole - 3 - yl] - 4 - (4 - methyl piperazine - 1 - yl) benzamide synthesis method

The invention belongs to the technical field of medicine and relates to a preparation method for PHA739358(Danusertib), i.e., (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide. According to the invention, altogether four reaction routes are designed, simple and easily available glycine is used as a raw material, reactions like addition, esterification, amino protection and cyclization are carried out so as to prepare (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide, yield of the route 1, 2 and 4 is more than 25%, respectively, and yield of the route 3 is more than 20%. The preparation method has the advantages of a few reaction steps, simple and convenient post-treatment operation, little time consumption, high yield and low total cost. Thus, a novel method is provided for preparation of the antitumor drug PHA739358.

Gemifloxacin intermediate preparation method

The invention relates to medicine and related fields, and especially relates to a gemifloxacin intermediate preparation method. According to the invention, acrylonitrile and ethyl glycinate hydrochloride are adopted as initial raw materials; through the processes of a nucleophilic addition reaction, amino protection, condensation, reduction protection, oxidation, oximation and deprotection, the gemifloxacin branched-chain intermediate 4-aminomethylpyrrolidin-3-one-O-methyloxime dihydrochloride is obtained. The route is simple; two steps of reactions are eliminated; raw materials are cheap and easy to obtain; and product yield is high. The route does not need column chromatography separation. The method provides a feasible synthesis route for industrial production.

Structure-activity-relationship of amide and sulfonamide analogs of omarigliptin

A series of novel substituted-[(3R)-amino-2-(2,5-difluorophenyl)]tetrahydro-2H-pyran analogs have been prepared and evaluated as potent, selective and orally active DPP-4 inhibitors. These efforts lead to the discovery of a long acting DPP-4 inhibitor, omarigliptin (MK-3102), which recently completed phase III clinical development and has been approved in Japan.

Design and synthesis of 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and pyrazolo[3,4-b]pyridines for Aurora-A kinase inhibitors

Two series of 3-aminopyrazole compounds including 24 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and 16 pyrazolo[3,4-b]pyridines were synthesized and evaluated against HCT116, A549, and A2780 tumor cell lines. Among them, three compounds were found to have the ideal anti-proliferative activities in vitro. Docking experiments showed that the novel pyrazolo[3,4-b]pyridines share the similar interaction mode with Aurora-A kinase as PHA739358.

Synthesis and in vitro antibacterial activity of fluoroquinolone derivatives containing 3-(N′-alkoxycarbamimidoyl)-4-(alkoxyimino) pyrrolidines

A series of novel 7-[3-(N′-alkoxycarbamimidoyl)-4-(alkoxyimino) pyrrolidin-1-yl] fluoroquinolone derivatives were designed, synthesized and characterized by 1H NMR, MS and HRMS. These fluoroquinolones were screened for their in vitro antibacter

Potent and selective aurora inhibitors identified by the expansion of a novel scaffold for protein kinase inhibition

Potent and selective Aurora kinase inhibitors were identified from the combinatorial expansion of the 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole bi-cycle, a novel and versatile scaffold designed to target the ATP pocket of protein kinases. The most potent c