methyl 1,2,3,4-tetrahyro-4-hydroxymethyl-β-carboline-2-carbodithioate | 102991-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 1,2,3,4-tetrahyro-4-hydroxymethyl-β-carboline-2-carbodithioate
• 英文别名: methyl (4RS)-4-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate；methyl 4-(hydroxymethyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbodithioate
• CAS: 102991-31-1
• 化学式: C₁₄H₁₆N₂OS₂
• 分子量: 292.426
• InChiKey: VNSIKXRDZFGWQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二硫化碳 、 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-4-ylmethanol 、 碘甲烷 在 三乙胺 作用下， 生成 methyl 1,2,3,4-tetrahyro-4-hydroxymethyl-β-carboline-2-carbodithioate
  参考文献：
  名称：

  Synthesis of 1,2,3,4-tetrahydro-.BETA.-carboline derivatives as hepatoprotective agents. IV. Positional isomers of 1,2,3,4-tetrahydro-2-methylthiothiocarbonyl-.BETA.-carboline-3-carboxylic acid and its 1-alkylated derivatives.

  摘要：

  合成了两种四氢-β-咔啉-1和-4-羧酸（1b，c）及相应的羟甲基衍生物（2b，c），它们是3-羧酸（1a）及其3-羟甲基衍生物（2a）的位置异构体，并测试了它们对四氯化碳（CCl4）诱导的小鼠肝损伤的保肝活性。这些位置异构体的保肝活性依次降低：1a>1b>1c>和2a>2b>2c。顺式和反式异构体（5a、b-14a、b）也检测了 1a 和 2a 1 位上烷基取代的影响。带有小烷基（如 Me 和 Et）的化合物显示出强大的活性。烷基加长一般会导致活性降低。在一系列 3-羧酸立体异构体（5a、b-9a、b）中，顺式异构体的活性往往高于反式异构体。

  DOI：

  10.1248/cpb.35.3705

文献信息

• Tetrahydro-.beta.-carboline derivatives
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04625032A1

  公开（公告）日：1986-11-25

  Tetrahydro-.beta.-carboline derivative of the formula: ##STR1## wherein R.sup.2 is lower alkyl, and either (A) R.sup.1 is hydroxymethyl or carboxy, R.sup.3 and R.sup.4 are both hydrogen, and X is halogen, lower alkyl, lower alkoxy, hydroxy or benzyloxy; or (B) R.sup.1 is hydrogen, carboxy-lower alkyl or a group of the formula: --CH.sub.2 OY, Y is lower alkyl, lower alkanoyl or an oxygen-containing monocyclic heterocyclic group, R.sup.3 is hydrogen, hydroxy-lower alkyl or carboxy, R.sup.4 is hydrogen or hydroxy-lower alkyl, and X is hydrogen, or a salt thereof, which has excellent activities for alleviating, curing and preventing hepatic damages and is useful as a therapeutic or prophylactic agent for hepatic diseases.

  Tetrahydro-.beta.-carboline衍生物的化学式：##STR1##其中R.sup.2为低级烷基，且（A）R.sup.1为羟甲基或羧基，R.sup.3和R.sup.4均为氢，X为卤素，低级烷基，低级烷氧基，羟基或苄氧基；或（B）R.sup.1为氢，羧基-低级烷基或式：--CH.sub.2 OY的基团，其中Y为低级烷基，低级烷酰基或含氧的单环杂环基团，R.sup.3为氢，羟基-低级烷基或羧基，R.sup.4为氢或羟基-低级烷基，X为氢，或其盐。该化合物具有优异的缓解、治疗和预防肝脏损伤的活性，可作为治疗或预防肝脏疾病的治疗药物或预防药物。
• SAIGA, YUTAKA;IIJIMA, IKUO;ISHIDA, AKIHIKO;MIYAGISHIMA, TOSHIKAZU;TAKAMUR+, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3705-3712
  作者：SAIGA, YUTAKA、IIJIMA, IKUO、ISHIDA, AKIHIKO、MIYAGISHIMA, TOSHIKAZU、TAKAMUR+

  DOI：——

  日期：——
• Synthesis of 1,2,3,4-tetrahydro-.BETA.-carboline derivatives as hepatoprotective agents. IV. Positional isomers of 1,2,3,4-tetrahydro-2-methylthiothiocarbonyl-.BETA.-carboline-3-carboxylic acid and its 1-alkylated derivatives.
  作者：YUTAKA SAIGA、IKUO IIJIMA、AKIHIKO ISHIDA、TOSHIKAZU MIYAGISHIMA、NORIO TAKAMURA、TOKURO OH-ISHI、MAMORU MATSUMOTO、Yuzo MATSUOKA

  DOI：10.1248/cpb.35.3705

  日期：——

  Two tetrahydro-β-carboline-1-and-4-carboxylic acids (1b, c) and the corresponding hydroxymethyl derivatives (2b, c), which are positional isomers of the 3-carboxylic acid (1a) and its 3-hydroxymethyl derivative (2a), were synthesized and tested for hepatoprotective activity against carbon tetrachloride (CCl4) -induced liver damage in mice. The hepatoprotective activity of these positional isomers decreased in the following order;1a> 1b> 1c> and 2a > 2b>2c. The effect of alkyl substitution at the 1 position of 1a and 2a was also examined with the cis and trans isomers (5a, b-14a, b). Compounds with small alkyl groups such as Me and Et showed potent activity. Lengthening of the alkyl group generally caused a decrease in activity. In a series of the stereoisomers of the 3-carboxylic acids (5a, b-9a, b), the cis isomers tend to be more active than the trans counterparts.

  合成了两种四氢-β-咔啉-1和-4-羧酸（1b，c）及相应的羟甲基衍生物（2b，c），它们是3-羧酸（1a）及其3-羟甲基衍生物（2a）的位置异构体，并测试了它们对四氯化碳（CCl4）诱导的小鼠肝损伤的保肝活性。这些位置异构体的保肝活性依次降低：1a>1b>1c>和2a>2b>2c。顺式和反式异构体（5a、b-14a、b）也检测了 1a 和 2a 1 位上烷基取代的影响。带有小烷基（如 Me 和 Et）的化合物显示出强大的活性。烷基加长一般会导致活性降低。在一系列 3-羧酸立体异构体（5a、b-9a、b）中，顺式异构体的活性往往高于反式异构体。