9-(prop-2-yn-1-yl)-2,3,4,9-tetrahydro-1H-carbazole | 79629-22-4

• 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: 9-(prop-2-yn-1-yl)-2,3,4,9-tetrahydro-1H-carbazole
• 英文别名: 1,2,3,4-tetrahydro-9(2-propynyl)-9H-carbazole；1,2,3,4-tetrahydro-9-(2-propynyl)-9H-carbazole；9-prop-2-ynyl-1,2,3,4-tetrahydrocarbazole
• CAS: 79629-22-4
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: YJNXZXJVWQOHSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(prop-2-yn-1-yl)-2,3,4,9-tetrahydro-1H-carbazole 、 丙酮 以58%的产率得到
  参考文献：
  名称：

  DARBINYAN EH. G.; POGOSYAN A. S.; MAXMUDYAN A. X., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1981, 34, HO 6, 495-499

  摘要：

  DOI：
• 作为产物：
  描述：

  N-prop-2-ynyl-N-phenylhydrazine 、 环己酮 以62%的产率得到
  参考文献：
  名称：

  DARBINYAN EH. G.; POGOSYAN A. S.; MAXMUDYAN A. X., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1981, 34, HO 6, 495-499

  摘要：

  DOI：

文献信息

• Triazolo(4,3-A)(1,4)benzodiazepines and thieno
  申请人：Hoffmann-La Roche Inc.

  公开号：US04959361A1

  公开（公告）日：1990-09-25

  The invention relates to compounds of the formula ##STR1## wherein X is --CH.dbd.CH-- or S; R.sub.1 is lower alkyl, lower alkoxy or trifluoromethyl; R.sub.2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or alkanoyloxy; R.sub.3 and R.sub.4, independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R.sub.2 cannot be hydroxy, lower alkoxy or alkanoyloxy; R.sub.5 is a radical of the formula R.sub.6 --(CH.sub.2).sub.n -- or R.sub.7 --O--(CH.sub.2).sub.m -- wherein R.sub.6 and R.sub.7 are aryl or a heterocyclic radical, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R.sub.6 must be attached through a carbon to carbon bond, and provided that R.sub.7 is always attached through a carbon to oxygen bond, and, when at least one asymmetric carbon is present, its enantiomers and racemates, and pharmaceutically acceptable acid addition salts thereof. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characterized by excess platelet activating factor or for the prevention and treatment of cardiovascular diseases, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.

  本发明涉及公式##STR1##的化合物，其中X为--CH.dbd.CH--或S；R.sub.1为较低的烷基，较低的烷氧基或三氟甲基；R.sub.2为氢，较低的烷基，较低的烷氧基，羟基或脂肪酰氧基；R.sub.3和R.sub.4分别为氢，氯，氟，较低的烷基或较低的烷氧基；s为0至1的整数，但当s为1时，R.sub.2不能为羟基，较低的烷氧基或脂肪酰氧基；R.sub.5为公式R.sub.6 --(CH.sub.2).sub.n --或R.sub.7 --O--(CH.sub.2).sub.m --的基团，其中R.sub.6和R.sub.7为芳基或杂环基，n为0至2的整数，m为1至2的整数，但当n为0时，R.sub.6必须通过碳与碳键连接，且当至少存在一个不对称碳时，其对映异构体和外消旋体以及药学上可接受的酸加合物盐。公式I的化合物表现出血小板活化因子（PAF）拮抗剂的活性，因此在具有过多血小板活化因子的疾病状态或用于预防和治疗心血管疾病，肺部疾病，免疫障碍，炎症性疾病，皮肤疾病，休克或移植排斥反应等方面有用。
• Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents
  作者：Dongamanti Ashok、Gugulothu Thara、Bhukya Kiran Kumar、Gundu Srinivas、Dharavath Ravinder、Thumma Vishnu、Madderla Sarasija、Bujji Sushmitha

  DOI：10.1039/d2ra05960f

  日期：——

  3-triazolylmethyl indole derivatives 4(a–u) was synthesized by rationally incorporating a pharmacophoric active heterocyclic ring containing indole and triazole moieties in one molecular frame via the conventional and microwave irradiation methods. Briefly, the new compounds 4(a–u) were synthesized via the N-alkylation of tetrahydro-1H-carbazoles followed by click reaction and copper-catalyzed Huisgen [3 + 2] cycloaddition

  在此，通过常规和微波辐射方法在一个分子框架中合理地结合含有吲哚和三唑部分的药效活性杂环，合成了一系列新的N-取代的 1,2,3-三唑基甲基吲哚衍生物4(a–u) . 简而言之，新化合物4(a–u)是通过四氢-1 H-咔唑的N-烷基化，然后在硫酸铜和抗坏血酸钠存在下进行点击反应和铜催化的 Huisgen [3 + 2] 环加成反应合成的各种芳香族叠氮化物3(a–m)。所有新合成的化合物都通过表征 1 H 和13 C NMR、质谱和红外光谱，并评估了它们的抗菌、抗氧化和抗癌活性。在合成的化合物中， 4d、 4j、 4n、 4p、 4s和4r被发现具有良好的抗菌、抗氧化和抗癌活性。通过针对靶受体 caspase-3 和 17-β-羟基类固醇脱氢酶 1 型的分子对接研究，进一步补充了合成化合物的生物活性，表明所报道的结构最适合靶分子的活性位点口袋。
• Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor
  作者：Armin Walser、Thomas Flynn、Carl Mason、Herman Crowley、Catherine Maresca、Bob Yaremko、Margaret O'Donnell

  DOI：10.1021/jm00107a048

  日期：1991.3

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.
• WALSER, ARMIN;FLYNN, THOMAS;MASON, CARL;CROWLEY, HERMAN;MARESCA, CATHERIN+, J. MED. CHEM., 34,(1991) N, C. 1209-1221
  作者：WALSER, ARMIN、FLYNN, THOMAS、MASON, CARL、CROWLEY, HERMAN、MARESCA, CATHERIN+

  DOI：——

  日期：——
• WALSER, ARMIN
  作者：WALSER, ARMIN

  DOI：——

  日期：——