Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: a tool for combinatorially developing peptidomimetics

Banfi, Luca; Guanti, Giuseppe; Riva, Renata

doi:10.1016/s0957-4166(99)00371-7

Cited by 13 publications

(19 citation statements)

References 57 publications

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“…> 95%) supported on celite, according to our previously reported protocol. 22,23 The enantiodivergency of these monoacetates should allow the independent conversion of them into both enantiomers of the desired isocyanides through an appropriate choice of the order of introduction of the needed functionalities.…”

Section: Resultsmentioning

confidence: 99%

“…A solution of (R)-or (S)-19 (123 mg, 306 mmol) in dry CH 2 Cl 2 (2.5 mL) was cooled to -30 (8.5), 326 (43), 301 (6.5), 299 (6.7), 271 (12), 269 (11), 259 (11), 257 (10), 233 (5.0), 232 (14), 231 (100), 230 (15), 229 (96), 220 (7.7), 187 (23), 185 (24), 180 (6.0), 179 (5.5), 157 (14), 155 (14), 151 (5.1), 150 (9.4), 149 (7.9), 146 (6.5), 139 (9.7), 137 (9.6), 135 (12), 131 (6.0), 127 (9.9), 115 (13), 114 (24), 99 (9.4), 89 (6.7), 86 (5.0), 85 (11), 84 (39), 78 (5.4), 77 (7.3), 76 (20), 75 (34), 74 (6.0), 73 (46), 71 (11), 64 (5.2), 63 (6.7), 59 (25), 58 (10), 57 (12), 55 (5.7), 53 (5.1), 47 (6.6), 45 (12), 43 (14), 41 (37), 39 (10). m/z (ESI+) 406.0795 (M + Na + ).…”

Section: (R)-or (S)-1-(tert-butyl)dimethylsilyloxy-2-((3-bromophenoxy...mentioning

confidence: 99%

“…Compound 20 was prepared from 11, following the procedure reported for compound (8.4), 155 (7.3), 126 (22), 110 (8.4), 109 (96), 108 (9.5), 96 (12), 95 (30), 93 (18), 83 (34), 82 (23), 81 (61), 80 (5.3), 79 (18), 77 (11), 76 (9.4), 75 (6.5), 71 (16), 70 (9.3), 69 (37), 68 (8.6), 67 (100), 65 (12), 64 (5.6), 63 (7.9), 59 (11), 57 (37), 56 (8.5), 55 (85), 54 (5.4), 53 (18), 43 (69), 41 (75), 39 (23) (15), 172 (16), 157 (8.4), 155 (7.2), 110 (10), 109 (19), 108 (9.8), 96 (12), 95 (35), 94 (7.1), 93 (10), 82 (19), 81 (48), 80 (18), 79 (18), 77 (9.9), 76 (8.3), 75 (6.3), 70 (10), 69 (16), 68 (23), 67 (51), 65 (12), 64 (6.4), 63 (9.4), 56 (15), 55 (100), 54 (9.9), 53 (20), 50 (5.5), 43 (32), 42 (11), 41 (72), 39 (25). m/z (ESI+) 346.0543 (M + Na + ).…”

Section: (Se)-2-((3-bromophenoxy)methyl)-5-methylhex-3-en-1-ol 20mentioning

confidence: 99%

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Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

et al. 2012

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A highly diastereoselective Ugi reaction involving a chiral cyclic imine, two enantiomerically pure isocyanides and various carboxylic acids was employed for the synthesis of polyfunctionalized pyrrolidines. Both chiral substrates have been efficiently prepared by chemoenzymatic methodologies from readily available achiral substrates. This highly convergent approach can find an application in the fragment-based drug discovery process.

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Section: Resultsmentioning

confidence: 99%

Section: (R)-or (S)-1-(tert-butyl)dimethylsilyloxy-2-((3-bromophenoxy...mentioning

confidence: 99%

Section: (Se)-2-((3-bromophenoxy)methyl)-5-methylhex-3-en-1-ol 20mentioning

confidence: 99%

See 1 more Smart Citation

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

et al. 2012

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“…1, 3-diaminopropane has been shown as an active crosslinking agent and can be involved into the biomaterial fabrications. It also has been used in many chemical reactions including biological compounds (Banfi et al, 1999) and drug delivery system (Kasuya et al, 2001). 5-FU and HT-29 cells from human colon adenocarcinoma cell line were used as the therapeutic drug and cancer cell, respectively.…”

Section: Introductionmentioning

confidence: 99%

Targeted delivery of 5-fluorouracil to HT-29 cells using high efficient folic acid-conjugated nanoparticles

Wang

Chen

et al. 2014

Drug Delivery

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The incorporation of a high percentage of targeting molecules into drug delivery system is one of the important methods for improving efficacy of targeting therapeutic drugs to cancer cells. PLGA-based drug delivery carriers with folic acid (FA) as targeting molecule have a low targeting efficiency due to a low FA conjugation ratio. In this work, we fabricated a FA-conjugated PLGA system using a crosslinker 1, 3-diaminopropane and have achieved a high conjugation ratio of 46.7% (mol/mol). The as-prepared PLGA-based biomaterial was used to encapsulate therapeutic drug 5-fluorouracil (5-FU) into nanoparticles. In the in vitro experiments, an IC₅₀ of 5.69 µg/mL has been achieved for 5-FU loaded PLGA-1, 3-diaminopropane-folic acid nanoparticles on HT-29 cancer cells and is significantly lower than that of 5-FU and 5-FU loaded PLGA nanoparticles which only have an IC₅₀ of 22.9 and 14.17 µg/mL, respectively. The fluorescent microscopy images showed that nanoparticles with FA are largely taken up by HT-29 cancer cells and the targeting nanoparticles have more affinity to cancer cells than the pure drugs and untreated nanoparticles. Therefore, the 1, 3-diaminopropane can facilitate the conjugation of FA to PLGA to form a novel polymer and 5-FU loaded PLGA-1, 3-diaminopropane-folic acid nanoparticles can be a highly efficient system for specific delivery of drugs to cancer cells.

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“…This FU loaded PLGA-1,3-diaminopropane folic acid nanoparticles (Fig. 8) are one of the efficient approaches to transfer the drug to tumor cells [66,68,69].…”

Section: Folic Acid-5-flurouracil Conjugated Nanoparticlesmentioning

confidence: 99%

Vitamin Drug conjugate: a systematic review of pharmacological potential

Bhole¹,

Shinde²,

Bonde³

et al. 2021

Bull. of the Kar. Univ. "Chem". Ser.

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Cancer is a chronic disease which can cause death. In traditional chemotherapycytotoxic drugs are used to kill proliferating cancer cells. The cytotoxic agent exhibits less specificity, less biological activity, causes sys-temic toxicity and undesirable side effects. Each year, about 1.8 million of the population are infected and die due to tuberculosis infection. An increase of drug resistance during the tuberculosis treatment is a significant concern. So, it is necessary to develop a new approach or therapies to resolve drug resistance, drug selectivity in tuberculosis infection and the reduction of the side effects of cytotoxic agents and anti-tubercular drugs. This review describes the newly emerging concept of «vitamin drug conjugate». Vitamin-drug conjugate is a specifically carried drug toward the target site, is one of the promising ways to treat chronic diseases like can-cer and tuberculosis and enhance the therapeutic outcome. The purpose of this review is to explore vitamin as a targeting moiety for new anticancer and anti-tubercular drug to overcome challenges, such as non-selectivity, systemic toxicity and multidrug resistance. This approach is beneficial in the treatment of life-threatening disease like cancer, tuberculosis and also in many viral infections.

show abstract

Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: a tool for combinatorially developing peptidomimetics

Cited by 13 publications

References 57 publications

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

Targeted delivery of 5-fluorouracil to HT-29 cells using high efficient folic acid-conjugated nanoparticles

Vitamin Drug conjugate: a systematic review of pharmacological potential

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