58123-62-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-D-Proline is used as a chiral building block for the synthesis of pharmaceuticals, leveraging its ability to induce asymmetric synthesis to create enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 1-Methyl-D-Proline is utilized as a chiral building block for the synthesis of agrochemicals, contributing to the development of more targeted and environmentally friendly products.
Used in Neurological Disorder Treatment:
1-Methyl-D-Proline is being studied for its potential use in the treatment of neurological disorders, given its presence in proteins and its potential interaction with biological systems, although further research is required to confirm its efficacy and safety in this application.
Used in Cancer Treatment Research:
1-Methyl-D-Proline is under investigation for its potential role in the treatment of certain types of cancers, with ongoing research aimed at understanding its biochemical properties and how it might contribute to therapeutic strategies against cancer.

Upstream product

• 50-00-0 formaldehyd 
• 7776-34-3 L-proline hydrochloride 
• 147-85-3 L-proline 
• 124-38-9 carbon dioxide 
• 265660-44-4 (2S)-(+)-N-methyl-2-tributylstannylpyrrolidine 
• 104097-12-3 1-methyl-3-(1-methyl-pyrrolidin-2-yl)-1H-pyridin-2-one 
• 7664-93-9 sulfuric acid 
• 67-56-1 methanol 
• 344-25-2 D-Prolin 
• 471-87-4 L-proline betaine 

Downstream Products

• 471-87-4 L-proline betaine 
• 34381-71-0 (S)-2-hydroxymethyl-1-methylpyrrolidine 
• 1024582-70-4 tert-butyl 5-(2-(3-((S)-1-methylpyrrolidine-2-carboxamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 1105044-40-3 (2S,2'S)-[(1S,2S)-1,2-bis(4-tert-butylphenyl)ethane-1,2-diyl] bis[1-methylpyrrolidine-2-carboxylate] 
• 1105044-36-7 (2S,2'S)-[(1S,2S)-1,2-diphenylethane-1,2-diyl] bis[1-methylpyrrolidine-2-carboxylate] 
• 1022161-75-6 (2S,2'S)-N,N'-[(1S,2S)-1,2-diphenylethane-1,2-diyl] bis(1-methylpyrrolidine-2-carboxamide) 
• 1105044-55-0 (2S,2'S)-N,N'-[(1R,2R)-1,2-diphenylethane-1,2-diyl] bis(1-methylpyrrolidine-2-carboxamide) 
• 1105044-39-0 (2S,2'S)-[(1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diyl] bis[1-methylpyrrolidine-2-carboxylate] 
• 1105044-38-9 (2S,2'S)-[(1S,2S)-1,2-bis(4-fluorophenyl)ethane-1,2-diyl] bis[1-methylpyrrolidine-2-carboxylate] 
• 1005784-67-7 N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1-methyl-L-prolinamide 
• 1095322-95-4 N-[1-(1-methyl-L-prolyl)piperidin-4-yl]-5-(phenylsulfonyl)-2-(trifluoromethyl)benzenesulfonamide hydrochloride 
• 1205601-86-0 (S)-1-Methyl-pyrrolidine-2-carboxylic acid {1-[1-benzyl-5-(4-fluoro-phenyl)-1H-[1,2,4]triazol-3-ylcarbamoyl]-1-methyl-ethyl}-amide 
• 1235841-51-6 (S)-N-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)-phenoxy)ethyl)-N,1-dimethylpyrrolidine-2-carboxamide 
• 1235841-59-4 (S)-N-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)-phenoxy)ethyl)-N-ethyl-1-methylpyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

Leonurine derivative and application thereof in preparing medicine for preventing or treating ischemic cerebrovascular diseases

The invention provides a leonurine derivative and application of the leonurine derivative in preparation of a medicine for preventing or treating ischemic cerebrovascular diseases. The leonurine derivative has a structure as shown in a general formula (I), wherein X is selected from O or NH; Y is selected from any one of natural amino acid, substituted amino acid or amino alcohol; Z is selected from H, proline and any substituted proline. Pharmacological experiments prove that the leonurine derivative provided by the invention has the effects of neuroprotection, cerebral infarction area reduction and animal neurobehavioral scoring, and is good in safety, so that the leonurine derivative has important significance for developing novel medicines for preventing or treating ischemic cerebrovascular diseases.

Design, synthesis, and biological evaluation of novel stachydrine derivatives as potent neuroprotective agents for cerebral ischemic stroke

Stachydrine is a natural product with multiple protective biological activities, including those involved in preventing cancer, ischemia, and cardiovascular disease. However, its use has been limited by low bioavailability and unsatisfactory efficacy. To address this problem, a series of stachydrine derivatives (A1/A2/A3/A4/B1/B2/B3/B4) were designed and synthesized, and biological studies were carried out in vitro and in vivo. When compared with stachydrine, Compound B1 exhibited better neuroprotective effects in vitro, and significantly reduced infarction size in the model of the middle cerebral artery occlusion rat model. Therefore, Compound B1 was selected for further research on ischemic stroke. [Figure not available: see fulltext.].

A Copper-Catalyzed Sonogashira Coupling Reaction of Diverse Activated Alkyl Halides with Terminal Alkynes Under Ambient Conditions

We describe a copper-catalyzed Sonogashira coupling reaction of alkyl halides with terminal alkynes under ambient conditions, efficiently providing a versatile tool for the construction of substituted alkynes. A new proline-based N,N,P-ligand is utilized to promote the transformation under a mild reaction condition. Diverse alkyl halides, such as primary and secondary (hetero)benzyl chlorides and bromides, secondary and tertiary α-bromo amides and propargylic bromide, are applicable to provide a wide array of alkynes. (Figure presented.).

MORPHINAN DERIVATIVE

A compound represented by the following general formula (I), wherein R1 represents hydrogen, C1-10 alkyl, cycloalkylalkyl where the cycloalkyl moiety has 3 to 6 carbon atoms and the alkylene moiety has 1 to 5 carbon atoms, or the like, R2 represents a 4- to 7-membered saturated heterocycle containing one or two heteroatoms which may be the same or different and are selected from N, O, and S, and two or more carbon atoms as ring-constituting atoms, the heterocycle may be substituted with a substituent such as an oxo group, R2 binds to Y via a carbon atom as a ring-constituting atom of R2, R3, R4, and R5, which are the same or different, represent hydrogen; hydroxy; or the like, R6a and R6b, which are the same or different, represent hydrogen or the like, R7 and R8, which are the same or different, represent hydrogen or the like, R9 and R10, which are the same or different, represent hydrogen or the like, X represents O or CH2, and Y represents C(= O) or the like), a tautomer of the compound, a stereoisomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate thereof is used as an anxiolytic, an antidepressant, or the like.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

Stachydrine derivative, preparation method thereof, and application thereof in preparation of cardiovascular and cerebrovascular disease treatment medicines

The invention provides a stachydrine derivative, a preparation method thereof, and an application thereof in the preparation of cardiovascular and cerebrovascular disease treatment medicines. The stachydrine derivative has a structure represented by general formula (I). The synthesis method comprises the following steps: carrying out a hydrogenation reaction on L-proline a and formaldehyde under the catalysis of a catalyst to prepare N-methyl-L-proline b; and carrying out a condensation reaction on the N-methyl-L-proline b and anthranilic acid, gamma-aminobutyramide, glutamine or glycine underthe action of dicyclohexylcarbodiimide (DCC) to prepare the stachydrine derivative B-1, B-2, B-3 or B-4. Pharmacologic experiments prove that the stachydrine derivative has a nerve protection effectand a cardiovascular and cerebrovascular disease treatment effect. The invention also provides the application of the stachydrine derivative in the preparation of the cardiovascular and cerebrovascular disease treatment medicines.

HEPATITIS C VIRUS INHIBITORS

The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: Green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

A series of l-phenylalanine ionic liquids (ILs), l-tyrosine ILs, tertiary amino analogues and proposed transformation products (PTPs) have been synthesised. Antimicrobial toxicity data, as part of the green chemistry metrics evaluation and to supplement preliminary biodegradation studies, was determined for ILs, tertiary amino analogues and PTPs. Good to very good overall yields (76 to 87%) for the synthesis of 6 ILs from l-phenylalanine were achieved. A C2-symmetric IL was prepared from TMS-imidazole in a one-pot two-step method in excellent yield (91%). Synthesis of the l-tyrosine IL derivatives utilised a simple protection group strategy by using an extra equivalent of the bromoacetyl bromide reagent. Improvements in the synthesis of the α-bromoamide alkylating reagent from l-phenylalanine were achieved, directed by green chemistry metric analysis. A solvent switch from dichloromethane to THF is described, however the yield was 15% lower. Antimicrobial activity testing of l-phenylalanine ILs, l-tyrosine ILs, tertiary amino analogues and PTPs, against 8 bacteria and 12 fungi strains, showed that no compound had a high antimicrobial activity, apart from an l-proline analogue. In this exceptional case, the highest toxicity (IC95 = 125 and 250 μM) was observed towards the two Gram positive strains Staphylococcus aureus and Staphylococcus epidermidis respectively. High antimicrobial activity was not found for the other bacteria or fungi strains screened. The limitations of the antimicrobial activity study is discussed in relation to SAR studies. Preliminary analysis of biodegradation data (Closed Bottle Test, OECD 301D) is presented. The pyridinium IL derivative is the preferred green IL of the series based on synthesis, toxicity and biodegradation considerations. This work is a joint study with Kümmerer and co-workers and the PTPs were selected as target compounds based on concurrent biodegradation studies by the Kümmerer group. For the comprehensive biodegradation and transformation product analysis see the accompanying paper.

Design, synthesis, and in vitro antiplasmodial activity of 4-aminoquinolines containing modified amino acid conjugates

Abstract: A new series of side chain-modified 4-aminoquinolines were synthesized and screened for in vitro antiplasmodial activity against both chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Among the series, compounds 30 and 31 showed significant inhibition of parasite growth against K1 strain of P. falciparum with IC50 values 0.28 and 0.31?μM, respectively, whereas compounds 34, 35, and 38 exhibited superior activity against K1 strain with IC50 values 0.18, 0.22, and 0.17?μM, respectively, as compared to 0.255?μM for chloroquine (CQ). All the compounds displayed good resistance factor between 1.54 and >34.48 as against 51.0 for CQ. All these analogues were found to form strong complex with hematin and inhibited the β-hematin formation in vitro, suggesting that this class of compounds act on a heme polymerization target. Overall results suggest that present series of compounds appear to be promising for further lead optimization to obtain compounds active against drug-resistant parasites. Graphical Abstract: [Figure not available: see fulltext.]

N-Methylation of Amines with Methanol at Room Temperature

N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups. (Chemical Presented)