Minoru Shindo

N-Carboxyphenyl)-4-chloroanthranilic acid disodium salt: a novel anti-arthritic agent without anti-inflammatory and immunosuppressive activities

Adjuvant arthritis in rats is well known as a chronic model of inflammation and has usually been employed in the evaluation of anti-arthritic drugs (Winter, 1965). Cell-mediated immunity is considered to be important for the development of adjuvant arthritis (Eugui & Houssay, 1975; Pearson & Wood, 1959, 1964; Waksman, Pearson & Sharp, 1960; Waksman & Wennersten, 1963). It has been reported that anti-inflammatory and immunosuppressive agents possess prophylactic or therapeutic activity in adjuvant arthritis (Winter, 1965; Glenn, 1966; Winter & Nuss, 1966; Currey & Ziff, 1968; Perper, Alvarez & others, 1971 ; Walz, DiMartino & Misher, 1971 ; Martel, Klicius & Herr, 1974). In this article we describe a new type of anti-arthritic agent, N-(2-carboxyphenyl)-4-chloroanthranilic acid disodium salt (CCA), which inhibits adjuvant arthritis in rats, in spite of its lack of both anti-inflammatory and immunosuppressive activities. Male Sprague-Dawley rats (8 weeks old) were purchased from Clea Japan, Inc. Adjuvant arthritis was induced by intradermal injection of 0.5 mg of heat-killed Mycobacterium tuberculosis cells suspended in liquid paraffin into the tails of rats.

Synthetic studies of vitamin D3 analogues from bile acids. Part 3. Syntheses of 1α,25-, 1α,24R-, and 1α,24S-dihydroxycholecalciferols from lithocholic acid and their biological activities

Syntheses of 1α,25-, 1α,24R-, and 1α,24S-dihydroxycholecalciferols from lithocholic acid via the analogous 1,4,6-trien-3-ones by application of Kanekos procedure are described. A new synthesis of 1α,25-dihydroxycholecalciferol from lithocholic acid via the 1,4-dien-3-one is also reported. The biological activities of the three cholecalciferols were tested.

Synthetic studies of vitamin D3 analogues from bile acids. Part 2. Syntheses of cholesta-1,4-dien- and -1,4,6-trien-3-ones having a 24-and/or 25-hydroxylated side chain from lithocholic acid

Syntheses of 3α-hydroxy-5β-cholestanes having a 25-, 24R-, or 24S-hydroxy group [(13), (6a and b)] or a 24,25-dihydroxy group [(14)] from lithocholic acid (1) are described. These hydroxylated cholestanes were converted to the 1,4-dien-3-ones (15), (10a and b), and (16), and then to the 1,4,6-trien-3-ones (18), (11a and b), and (19) by normal dehydrogenation procedures without affecting the side chains.

Synthesis of desmosterol and epidesmosterol from hyodeoxycholic acid

A new synthesis of desmosterol was described using hyodeoxycholic acid (3alpha,6alpha-dihydroxy-5beta-cholanic acid) as a starting material. Epidesmosterol (3alpha-hydroxycholesta-5,24-diene) was also synthesized for the first time from the same starting material.