Synthesis and Pharmacological Properties of 1-Substituted 3-Dimethylaminoalkoxy-1H-indazoles

Palazzo, G; Corsi, G. B.; Baiocchi, L.; Silvestrini, Bruno

doi:10.1021/jm00319a009

Cited by 45 publications

(32 citation statements)

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“…Herein, we wish to use a recent example to illustrate the importance of studying spermatogenesis, which can lead to exciting developments in a related field, such as male contraception. In the 1970s, there was an interest to develop male contraceptive drugs based on the core structure of indazole-3-carboxylic acid, such as lonidamine [1-(2,4-dichlorobenzyl)-indazole-3-carboxylic acid] (Palazzo et al 1966;Corsi & Palazzo 1976). In rodents, lonidamine and its analogues were shown to be potent compounds that induced spermatid loss from the seminiferous epithelium without affecting cell adhesion in other organs (Silvestrini 1981;Silvestrini et al 1984).…”

Section: Spermatogenesis: the Presentmentioning

confidence: 99%

The biology of spermatogenesis: the past, present and future

Cheng

Mruk

2010

Phil. Trans. R. Soc. B

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The physiological function of spermatogenesis in Caenorhabditis elegans, Drosophila melanogaster and mammals is to produce spermatozoa (1n, haploid) that contain only half of the genetic material of spermatogonia (2n, diploid). This half number of chromosomes from a spermatozoon will then be reconstituted to become a diploid cell upon fertilization with an egg, which is also haploid. Thus, genetic information from two parental individuals can be passed onto their offspring. Spermatogenesis takes place in the seminiferous epithelium of the seminiferous tubule, the functional unit of the mammalian testis. In mammals, particularly in rodents, the fascinating morphological changes that occur during spermatogenesis involving cellular differentiation and transformation, mitosis, meiosis, germ cell movement, spermiogenesis and spermiation have been well documented from the 1950s through the 1980s. During this time, however, the regulation of, as well as the biochemical and molecular mechanisms underlying these diverse cellular events occurring throughout spermatogenesis, have remained largely unexplored. In the past two decades, important advancements have been made using new biochemical, cell and molecular biology techniques to understand how different genes, proteins and signalling pathways regulate various aspects of spermatogenesis. These include studies on the differentiation of spermatogonia from gonocytes; regulation of spermatogonial stem cells; regulation of spermatogonial mitosis; regulation of meiosis, spermiogenesis and spermiation; role of hormones (e.g. oestrogens, androgens) in spermatogenesis; transcriptional regulation of spermatogenesis; regulation of apoptosis; cell -cell interactions; and the biology of junction dynamics during spermatogenesis. The impact of environmental toxicants on spermatogenesis has also become an urgent issue in the field in light of declining fertility levels in males. Many of these studies have helped investigators to understand important similarities, differences and evolutionary relationships between C. elegans, D. melanogaster and mammals relating to spermatogenesis. In this Special Issue of the Philosophical Transactions of the Royal Society B: Biological Sciences, we have covered many of these areas, and in this Introduction, we highlight the topic of spermatogenesis by examining its past, present and future.

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Section: Spermatogenesis: the Presentmentioning

confidence: 99%

The biology of spermatogenesis: the past, present and future

Cheng

Mruk

2010

Phil. Trans. R. Soc. B

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“…From the various conditions of their nucleophilic substitution reported in the literature (2 equiv. of nucleophile in dioxane, 5,6 1-1.2 equiv. of nucleophile in methanol or ethanol solution in the presence of potassium carbonate 3 , sodium acetate4 or triethyl amine, 9 1 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…1 Since many of them display a remarkable biological activity, their synthesis and transformations have been received particular interest for a long time. The 2-aryl-5-(substituted methyl)-1,3,4-oxadiazoles have been reported to show antibacterial, 2,3 antifungal, 4 analgesic and antiinflammatory 5,6 , and hypoglycemic 3 activity. Their synthetic usefulness has also been demonstrated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-(substituted-phenyl)-5-(aminomethyl)- and (thiomethyl)-1,3,4-oxadiazoles. Oxidation of thiomethyl-oxadiazole derivatives by dimethyldioxirane

Kiss‐Szikszai¹,

Patonay²,

Jekő³

2002

Arkivoc

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“…The indazole structural motif is found in various biological active molecules like compounds with antimicrobial and anti-inflammatory activity [1,2] or Eph receptor inhibitors [3]. Several functionalized 1H-indazole cores function as starting material for these pharmacologically relevant substances.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Molecular Structure of 2-(4-Methoxybenzyl)-4-nitro-2H-indazole

Ebert

Köckerling²,

Mamat

2012

Crystals

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Abstract:Two novel indazole derivatives protected with p-methoxybenzyl group were synthesized and characterized. The crystal and molecular structure of 2-(4-methoxybenzyl)-4-nitro-2H-indazole as one out of the two regioisomers is reported. The compound was obtained from a saturated petroleum ether/ethyl acetate mixture and crystallizes in the triclinic space group P1. The unit cell parameters are: a = 6.8994 (1) . There are two independent molecules found in the asymmetric unit.

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Synthesis and Pharmacological Properties of 1-Substituted 3-Dimethylaminoalkoxy-1H-indazoles

Cited by 45 publications

References 0 publications

The biology of spermatogenesis: the past, present and future

The biology of spermatogenesis: the past, present and future

Synthesis of 2-(substituted-phenyl)-5-(aminomethyl)- and (thiomethyl)-1,3,4-oxadiazoles. Oxidation of thiomethyl-oxadiazole derivatives by dimethyldioxirane

The Synthesis and Molecular Structure of 2-(4-Methoxybenzyl)-4-nitro-2H-indazole

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