5-(1,3-苯并噻唑-2-基)-1-戊胺 | 39650-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 5-(1,3-苯并噻唑-2-基)-1-戊胺
• 英文名称: 2-(5'-aminopentyl)-benzthiazole
• 英文别名: 5-(benzo[d]thiazol-2-yl)pentan-1-amine；5-(2-Benzothiazolyl)pentylamine；5-benzothiazol-2-yl-pentylamine；2-(5'-Aminopentyl)-benzthiazol；2-(5-Aminopentyl)-benzothiazol；2-Benzothiazolepentanamine；5-(1,3-benzothiazol-2-yl)pentan-1-amine
• CAS: 39650-67-4
• 化学式: C₁₂H₁₆N₂S
• 分子量: 220.338
• InChiKey: LRVUNUHOUQQGTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexanoic acid 、 5-(1,3-苯并噻唑-2-基)-1-戊胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以44%的产率得到N-(5-(benzo[d]thiazol-2-yl)pentyl)-6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexanamide
  参考文献：
  名称：

  Design, synthesis and neuroprotective evaluation of novel tacrine–benzothiazole hybrids as multi-targeted compounds against Alzheimer’s disease

  摘要：

  Alzheimer's disease (AD) is a multifactorial disorder with several target proteins contributing to its etiology. In search for multifunctional anti-AD drug candidates, taking into account that the acetylcholinesterase (AChE) and beta-amyloid (A beta) aggregation are particularly important targets for inhibition, the tacrine and benzothiazole (BTA) moieties were conjugated with suitable linkers in a novel series of hybrids. The designed compounds (7a-7e) were synthesized and in vitro as well as in ex vivo evaluated for their capacity for the inhibition of acetylcholinesterase (AChE) and A beta self-induced aggregation, and also for the protection of neuronal cells death (SHSY-5Y cells, AD and MCI cybrids). All the tacrine-BTA hybrids displayed high in vitro activities, namely with IC50 values in the low micromolar to sub-micromolar concentration range towards the inhibition of AChE, and high percentages of inhibition of the self-induced A beta aggregation. Among them, compound 7a, with the shortest linker, presented the best inhibitory activity of AChE (IC50 = 0.34 mu M), while the highest activity as anti-A beta(42) self-aggregation, was evidenced for compound 7b (61.3%, at 50 mu M. The docking studies demonstrated that all compounds are able to interact with both catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Our results show that compounds 7d and 7e improved cell viability in cells treated with A beta(42) peptide. Overall, these multi-targeted hybrid compounds appear as promising lead compounds for the treatment of Alzheimer's disease. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.028
• 作为产物：
  描述：

  2-氨基苯硫醇 、 6-氨基己酸 在 polyphosphoric acid 作用下， 反应 4.0h， 以75%的产率得到5-(1,3-苯并噻唑-2-基)-1-戊胺
  参考文献：
  名称：

  Design, synthesis and neuroprotective evaluation of novel tacrine–benzothiazole hybrids as multi-targeted compounds against Alzheimer’s disease

  摘要：

  Alzheimer's disease (AD) is a multifactorial disorder with several target proteins contributing to its etiology. In search for multifunctional anti-AD drug candidates, taking into account that the acetylcholinesterase (AChE) and beta-amyloid (A beta) aggregation are particularly important targets for inhibition, the tacrine and benzothiazole (BTA) moieties were conjugated with suitable linkers in a novel series of hybrids. The designed compounds (7a-7e) were synthesized and in vitro as well as in ex vivo evaluated for their capacity for the inhibition of acetylcholinesterase (AChE) and A beta self-induced aggregation, and also for the protection of neuronal cells death (SHSY-5Y cells, AD and MCI cybrids). All the tacrine-BTA hybrids displayed high in vitro activities, namely with IC50 values in the low micromolar to sub-micromolar concentration range towards the inhibition of AChE, and high percentages of inhibition of the self-induced A beta aggregation. Among them, compound 7a, with the shortest linker, presented the best inhibitory activity of AChE (IC50 = 0.34 mu M), while the highest activity as anti-A beta(42) self-aggregation, was evidenced for compound 7b (61.3%, at 50 mu M. The docking studies demonstrated that all compounds are able to interact with both catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Our results show that compounds 7d and 7e improved cell viability in cells treated with A beta(42) peptide. Overall, these multi-targeted hybrid compounds appear as promising lead compounds for the treatment of Alzheimer's disease. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.028

文献信息

• [EN] 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] DERIVES AMIDES DE L'ACIDE CARBOXYLIQUE DE 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE 3 ET COMPOSES ASSOCIES EN TANT QU'ANTAGONISTES DE RECEPTEUR DE B1 DE LA BRADYKININE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：ELAN PHARM INC

  公开号：WO2004098589A1

  公开（公告）日：2004-11-18

  Disclosed are compounds of formula I and II that are bradykinin B1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.

  公开的是化合物I和II的结构式，它们是激肽酶B1受体拮抗剂，适用于治疗哺乳动物中由激肽酶B1受体介导的疾病，或缓解与疾病状况相关的不良症状。其中某些化合物表现出增强的效力，并且预计还将表现出延长作用的特性。
• SUBSTITUTED PROPIONYL DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0949238A1

  公开（公告）日：1999-10-13

  The present invention relates to a compound represented by the following formula (1): [wherein, X1 represents a carboxyl group which may be esterified or the like group; Y1 represents a single bond, -O- or -N(R1)-; at least one of A1, A2 and A3 is a group represented by the following formula (2): -R2-a1-R3-a2 →wherein, R2 represents a divalent C2-12 hydrocarbon group, R3 represents a single bond or a divalent C1-12 hydrocarbon group, a1 and a2 individually represent a single bond, -S-, -SO-, -SO2-, -SO2NH-, -O-, -N(R4)-, -CON(R5)-, -C(=O)- or - Si(R6)(R7)- and → means bonding with Q1, Q2 or Q3}, the remaining one or two of A1, A2 and A3 are the same or different and each independently represents a group represented by the following formula (3): -R8-a3-R9-a4 →wherein, R8 and R9 individually represent a single bond or a divalent C1-12 hydrocarbon group, a3 and a4 individually represent a single bond, -S-, -SO-, -SO2-, -SO2NH-, -O-, - N(R10)-, -CON(R11)-, -C(=O)- or -SI(R12)(R13)- and → means bonding with Q1, Q2 or Q3},; at least one of Q1, Q2 and Q3 represents a cyclic hydrocarbon group or heterocyclic group and the remaining one or two of Q1, Q2 and Q3 individually represent a hydrogen atom, a carboxyl group which may be esterified, a hydrocarbon group or a heterocyclic group] or salt thereof; and a pharmaceutical comprising the same as an effective ingredient. The compound exhibits strong squalene synthetase inhibitory action and is therefore useful as a pharmaceutical for the treatment·prevention of hypercholesterolemia, hyperlipemia or arteriosclerosis.

  本发明涉及一种由以下式（1）表示的化合物：[其中，X1代表可能酯化或类似基团的羧基；Y1代表单键，-O-或-N（R1）-；A1、A2和A3中至少有一个是由以下式（2）表示的基团：-R2-a1-R3-a2 →其中，R2代表二价的C2-12碳氢基团，R3代表单键或二价的C1-12碳氢基团，a1和a2分别代表单键，-S-，-SO-，-SO2-，-SO2NH-，-O-，-N（R4）-，-CON（R5）-，-C（=O）-或-Si（R6）（R7）-，→表示与Q1、Q2或Q3结合}，A1、A2和A3中剩余的一个或两个是相同或不同的，并且每个独立地表示由以下式（3）表示的基团：-R8-a3-R9-a4 →其中，R8和R9分别代表单键或二价的C1-12碳氢基团，a3和a4分别代表单键，-S-，-SO-，-SO2-，-SO2NH-，-O-，-N（R10）-，-CON（R11）-，-C（=O）-或-SI（R12）（R13）-，→表示与Q1、Q2或Q3结合}；Q1、Q2和Q3中至少有一个代表环烃基或杂环烃基，剩余的一个或两个分别代表氢原子，可能酯化的羧基，碳氢基团或杂环烃基的其中一个或两个]或其盐；以及包括其作为有效成分的药物。该化合物表现出强烈的角鲨烯合酶抑制作用，因此可用作治疗高胆固醇血症、高脂血症或动脉硬化的药物。
• 2-Arylbenzothiazole derivatives
  申请人：Stevens Francis G. Malcolm

  公开号：US20060063816A1

  公开（公告）日：2006-03-23

  A compound of general structure I, wherein the compound is optionally in the form of an N-oxide or S-oxide or prodrug form and/or pharmaceutically acceptable salt thereof wherein: each of R 1 to R 9 is independently selected from hydrogen, hydroxyl, alkoxy, halo, mesyl, CX 3 (X=halo), —O(CH 2 )nNYZ—, substituted or unsubstituted lower alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; optionally R 6 and R 7 together form a dioxymethylene (—OCH 2 O—) unit and wherein n is 1 to 3 and Y and Z are independently selected from any of the following: C 1 -C 6 straight chain, branched or cyclic substituted or unsubstituted alkyl group, Y and Z can be taken together to form a cyclic alkyl or hetereoalkyl group wherein in addition to N the hetereoalkyl group comprises a heteroatom selected from N, O or S.

  通用结构I的化合物，其中该化合物可以是N-氧化物或S-氧化物或前药形式和/或其药用可接受盐形式，其中：R1至R9中的每一个独立地选择自氢、羟基、烷氧基、卤素、甲磺基、CX3（X=卤素）、—O(CH2)nNYZ—、取代或未取代的较低烷基、取代或未取代的杂烷基、取代或未取代的芳基或杂芳基，以及取代或未取代的芳基或杂芳基；可选地，R6和R7一起形成二氧亚甲基（—OCH2O—）单元，其中n为1至3，Y和Z分别选择自以下任一：C1-C6直链、支链或环状取代或未取代的烷基，Y和Z可以一起形成环状烷基或杂环烷基，其中除N外，杂环烷基还包括从N、O或S中选择的杂原子。
• Benzothiazolyl derivatives
  申请人：——

  公开号：US20040266845A1

  公开（公告）日：2004-12-30

  The present invention relates to compounds of formula (I) 1 wherein R 1 , R 2 , R 3° R 3a and R 3b are as provided in the description, and pharmaceutically acceptable salts thereof, for use in the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors such as obesity.

  本发明涉及式(I)1的化合物，其中R1、R2、R3°R3a和R3b如描述中所述，并且其药学上可接受的盐，用于治疗和/或预防与调节CB1受体相关的疾病，如肥胖。
• Process for preparing a 2(.omega.-aminoalkyl)-1,3-heterocyclic compounds
  申请人：Bayer Aktiengesellschaft

  公开号：US03972890A1

  公开（公告）日：1976-08-03

  2-(.omega.-AMINOALKYL)-1,3-HETEROCYCLIC COMPOUNDS ARE PREPARED BY REACTING A COMPOUND SELECTED FROM THE GROUP OF A DIAMINE, AN AMINOHYDROXY AND AN AMINOTHIOL COMPOUND, SAID COMPOUND HAVING THE FORMULA: ##EQU1## wherein ##EQU2## A is a bivalent chain of 2 or 3 carbon atoms, which can also be part of a bivalent, optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical, and X is oxygen, sulphur or the group ##EQU3## wherein R.sup.7 is as defined herein with a lactam having the formula ##EQU4## WHEREIN B is selected from the group of a single bond, oxygen, sulphur, the group ##EQU5## wherein R.sup.6 is as defined herein, and arylene, R.sup.1, r.sup.2, r.sup.3 and R.sup.4, which may be the same or different, are selected from the group of hydrogen, halogen, nitro and optionally substituted aliphatic, cycloaliphatic, araliphatic and aromatic, R.sup.5, r.sup.6 and R.sup.7, which may be the same or different, are selected from the group of hydrogen and optionally substituted aliphatic, cycloaliphatic, araliphatic and aromatic, and n and m, which may be the same or different, are intergers of from 1 to 14, with the proviso that the sum of n and m does not exceed 15, At a temperature of from 100.degree. to 300.degree.C in the presence of at least a catalytic quantity of an acid and/or an acid catalyst.

  通过反应选择自二胺、氨基羟基和氨基硫化物化合物的群组中的化合物制备2-(.omega.-AMINOALKYL)-1,3-杂环化合物，所述化合物具有以下公式：##EQU1## 其中##EQU2## A是2或3个碳原子的双价链，也可以是双价的、可选地取代的脂肪、环脂肪、芳基或芳香族基团的一部分，X是氧、硫或##EQU3##团，其中R.sup.7如本文所定义，与式为##EQU4##的内酰胺反应，其中B来自单键、氧、硫、##EQU5##团，其中R.sup.6如本文所定义，和芳基，R.sup.1、r.sup.2、r.sup.3和R.sup.4可以是相同或不同的氢、卤素、硝基和可选的取代脂肪、环脂肪、芳基和芳香族基团，R.sup.5、r.sup.6和R.sup.7可以是相同或不同的氢和可选的取代脂肪、环脂肪、芳基和芳香族基团，n和m可以是1到14的整数，但n和m的和不得超过15，在至少一种酸和/或酸催化剂的催化下，在100℃至300℃的温度下进行反应。