Osteoblast: | Osteoclast: |

Fig. 7 Biologically active 1-hydroxyindoles and analogs (1)

It is important to note that in these compounds the activity depends on the length of the Nb-alkyl side chain: the longer the side chain the stronger the activity [46,47].

In our project to develop a drug for osteoporosis, we have created 1-hydroxytryptophan ((dl)-41) and 1-hydroxytryptamine derivatives (52, 185, and 30). Among them, (dl)-41 and 52 have the same trend not only to stimulate osteoblasts, but also to suppress osteoclast activity in the cultured scales of goldfish [48,49]. On the other hand, compounds (185 and 30 suppress both osteoblasts and osteoclasts. During the study, we have succeeded in creating potent and promising compounds for osteoporosis [50,51].

From the point of view of developing an anti-cancer drug, some potent 1-hydroxyindole derivatives have been discovered through the test using human tumor cells. Further study is in progress (Somei and co-workers, personal communication, 2006).

An attempt at developing an antifungal drug leads us to find 1-hydroxy-(200) and 1-methoxyindole derivatives (201a,b, 202, and 203) as shown in Fig. 8 (Somei and co-workers, personal communication, 2006). These have activity against gram-negative bacteria; Erwinia carotovora and Xanthomonas oryza. They also have mild activity against filamentous fungi; Pythium de-baryanum, Phytophthora infestans, Pyricularia oryzae, Botrytis cinerea, and Rhizoctonia solani. Compounds (204a,b) are active against Erwinia carotovora and 204a is more potent than 204b. As for the inhibition of IAA-induced ethylene formation with the rice seedling test, compound (205) shows weak activity.

Phytoalexin is also an interesting compound. The plant family, Cruciferae, utilizes 1-methoxyindole compounds as phytoalexins. We expected there was a chance to find new agrochemicals among analogs of 1-methoxyindole-3-carbaldehyde [52] (10a, daikon-phytoalexin [53]). So, we have thus far prepared a lot of related compounds. Some of them are 5a,b, 6a-f, 10b, 119, 206a-d, 207a,b, and 208a,b. These are found to have mild activities (Somei and co-workers, personal communication, 2006).

Melatonin (64) is a hormone secreted from the pineal gland and is well known to control the circadian rhythms. Its multimodality of biological activities [49,54-59] has led us to synthesize unprecedented 1-hydroxy- (161) and 1-methoxymelatonin (209a) from melatonin [26] as lead compounds for new drugs [46,47,50,51]. Quite recently, Tsotinis and co-workers reported its analogs (209b,c) as melatonin receptor agonists [60].

We have been engaged in a project for a long time aimed at increasing the harvest of farm products. During this study, we have discovered that 4-iodoindole-3-carbaldehydes (210a-c), 2-bromoindole-3-carbaldehydes (211a-c), 2-(3-hydroxy-3-methylbuten-1-yl)indole-3-carbaldehydes (212a-c), and 2-(3-hydroxy-3-methylbuten-1-yl)-3-(2-nitrovinyl)indoles (213a-c) are potent plant-growth regulators and promote root growth of various plants (Somei and co-workers, personal communication, 2006). 1-Methoxy analogs i^COOMe

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