1-苯甲酰基-4-(1H-吲哚-3-基)哌啶 | 56361-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯甲酰基-4-(1H-吲哚-3-基)哌啶
• 英文名称: (4-(1H-indol-3-yl)piperidin-1-yl)(phenyl)methanone
• 英文别名: 1-benzoyl-4-indol-3-yl-piperidine；1-benzoyl-4-(1H-indol-3-yl)piperidine；1-Benzoyl-4--piperidin；[4-(1H-indol-3-yl)piperidin-1-yl]-phenylmethanone
• CAS: 56361-85-4
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: YTURLADWFKSLFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  220-222 °C
• 沸点：
  533.7±43.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 溶剂黄146 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.17h， 生成 1-苯甲酰基-4-(1H-吲哚-3-基)哌啶
  参考文献：
  名称：

  Exploring the 3-piperidin-4-yl-1H-indole scaffold as a novel antimalarial chemotype

  摘要：

  A series of 3-piperidin-4-yl-1H-indoles with building block diversity was synthesized based on a hit derived from an HTS whole-cell screen against Plasmodium falciparum. Thirty-eight compounds were obtained following a three-step synthetic approach and evaluated for anti-parasitic activity. The SAR shows that 3-piperidin-4-yl-1H-indole is intolerant to most N-piperidinyl modifications. Nevertheless, we were able to identify a new compound (10d) with lead-like properties (MW = 305; cLogP = 2.42), showing antimalarial activity against drug-resistant and sensitive strains (EC50 values similar to 3 mu M), selectivity for malaria parasite and no cross-resistance with chloroquine, thus representing a potential new chemotype for further optimization towards novel and affordable antimalarial drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.047

文献信息

• Synthesis of piperidine derivatives with a quinazoline ring system as potential antihypertensive agents.
  作者：HARUKI TAKAI、HIROYUKI OBASE、MASAYUKI TERANISHI、AKIRA KARASAWA、KAZUHIRO KUBO、KATSUICHI SHUTO、YUTAKA KASUYA、KOKI SHIGENOBU

  DOI：10.1248/cpb.34.1907

  日期：——

  A series of piperidine derivatives with a 2-oxo-1, 2, 3, 4-tetrahydro-quinazoline or 2, 4-dioxo-1, 2, 3, 4-tetrahydroquinazoline ring at the 4-position were prepared and tested for antihypertensive activity. Among the compounds tested, 1-[2-hydroxy-2-(3, 4-methylenedioxyphenyl)ethyl]-4-(2, 4-dioxo-1, 2, 3, 4-tetrahydro-3-quinazolinyl)piperidine (20) and 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-4-(2-oxo-1, 2, 3, 4-tetrahydro-3-quinazolinylmethyl)piperidine (30) produced relatively strong hypotension in the spontaneously hypertensive rat model.

  一系列以2-氧代-1, 2, 3, 4-四氢喹唑啉或2, 4-二氧代-1, 2, 3, 4-四氢喹唑啉环在4位的哌啶衍生物被合成并测试了其抗高血压活性。在测试的化合物中，1-[2-羟基-2-(3, 4-亚甲基二氧基苯基)乙基]-4-(2, 4-二氧代-1, 2, 3, 4-四氢-3-喹唑啉基)哌啶（20）和1-[2-(4-氯苯基)-2-羟基乙基]-4-(2-氧代-1, 2, 3, 4-四氢-3-喹唑啉基甲基)哌啶（30）在自发性高血压大鼠模型中产生了相对较强的降压效果。
• TRYPTOPHAN-2,3-DIOXYGENASE (TDO) AND/OR INDOLAMINE-2,3-DIOXYGENASE (IDO) INHIBITORS AND THEIR USE
  申请人：Iomet Pharma Ltd.

  公开号：EP3082802B1

  公开（公告）日：2020-02-26
• Pharmaceutical Compound
  申请人：IOMET PHARMA LTD

  公开号：US20160367564A1

  公开（公告）日：2016-12-22

  Provided is a tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO) inhibitor compound for use in medicine, which compound comprises the following formula: wherein X 2 , X 4 , X 10 , and X 11 may be the same or different and each is independently selected from C and N; X 1 , X 3 , X 5 , X 6 , X 7 , X 8 , and X 9 may be the same or different and each is independently selected from C, N and O; each bond having a dotted line may independently be a double bond or a single bond, provided that valencies at each atom are maintained; the dotted lines joining X 4 with the carbon atoms either side of X 2 are single bonds, and are only present when X 2 is absent, X 3 is absent and X 4 is C, and when these bonds are present the ring carbons on each side of X 2 are not directly bonded to each other; each R 1 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of R 1 groups present is such that the valency of X 1 is maintained; each R 12 , R 13 , R 13′ , R 14 , R 15 and R 15′ may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valency of the ring carbon atoms is maintained; R 16 may be present or absent and is selected from H and a substituted or unsubstituted organic group, provided that the number of R 16 groups present is such that the valency of X 2 is maintained; each R 17 may be present or absent and may be the same or different and is independently selected from H and a substituted or unsubstituted organic group, provided that the number of R 17 groups present is such that the valency of X 3 is maintained; each R 2 , R 3 , R 4 , and R 5 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valencies of X 6 , X 7 , X 8 , and X 9 are maintained; each R 7 , R 8 and R 9 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valencies of X 10 , X 11 , and X 5 are maintained; and R 6 is selected from H and a substituted or unsubstituted organic group, preferably H and a substituted or unsubstituted C 1 -C 6 alkyl group; and wherein any R group may form a ring with any other R group on an adjacent and/or proximal atom.
• US9931347B2
  申请人：——

  公开号：US9931347B2

  公开（公告）日：2018-04-03
• [EN] PHARMACEUTICAL COMPOUND<br/>[FR] COMPOSÉ PHARMACEUTIQUE
  申请人：IOMET PHARMA LTD

  公开号：WO2015082499A2

  公开（公告）日：2015-06-11

  Provided is a tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO) inhibitor compound for use in medicine, which compound comprises the following formula: wherein X2, X4, X10, and X11 may be the same or different and each is independently selected from C and N; X1, X3, X5, X6, X7, X8, and X9 may be the same or different and each is independently selected from C, N and O; each bond having a dotted line may independently be a double bond or a single bond, provided that valencies at each atom are maintained; the dotted lines joining X4 with the carbon atoms either side of X2 are single bonds, and are only present when X2 is absent, X3 is absent and X4 is C, and when these bonds are present the ring carbons on each side of X2 are not directly bonded to each other; each R1 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of R1 groups present is such that the valency of X1 is maintained; each R12, R13, R13', R14, R15 and R15 may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valency of the ring carbon atoms is maintained; R16 may be present or absent and is selected from H and a substituted or unsubstituted organic group, provided that the number of R16 groups present is such that the valency of X2 is maintained; each R17 may be present or absent and may be the same or different and is independently selected from H and a substituted or unsubstituted organic group, provided that the number of R17 groups present is such that the valency of X3 is maintained; each R2, R3, R4, and R5 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valencies of X6, X7, X8, and X9 are maintained; each R7, R8 and R9 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valencies of X10, X11, and X5 are maintained; and R6 is selected from H and a substituted or unsubstituted organic group, preferably H and a substituted or unsubstituted C1-C6 alkyl group; and wherein any R group may form a ring with any other R group on an adjacent and/or proximal atom.