2-[8-(1-ethoxycarbonyl-ethylsulfanyl)-octylsulfanyl]-propionic acid ethyl ester | 212771-43-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[8-(1-ethoxycarbonyl-ethylsulfanyl)-octylsulfanyl]-propionic acid ethyl ester
• 英文别名: Ethyl 2-[8-(1-ethoxy-1-oxopropan-2-yl)sulfanyloctylsulfanyl]propanoate
• CAS: 212771-43-2
• 化学式: C₁₈H₃₄O₄S₂
• 分子量: 378.598
• InChiKey: SNDUBMHWPXSPDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[8-(1-ethoxycarbonyl-ethylsulfanyl)-octylsulfanyl]-propionic acid ethyl ester 在 卫可 作用下， 以86%的产率得到2-[8-(1-carboxyl-ethylsulfonyl)-octane-1-sulfonyl]-propionic acid ethyl ester
  参考文献：
  名称：

  N-hydroxy-2-(Alkyl,Aryl or Heteroaryl sulfanyl, sulfinyl or sulfonyl) 3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors

  摘要：

  翻译结果如下： 基质金属蛋白酶（MMps）是一组与连接组织和基底膜病理破坏有关的酶。这些含有锌的内切肽酶包括几个酶亚组，如胶原酶、溶素和明胶酶。肿瘤坏死因子-α转化酶（TACE），一种促炎症细胞因子，催化膜结合的肿瘤坏死因子-α前体蛋白形成肿瘤坏死因子-α。因此，人们预期基质金属蛋白酶（MMPs）和TACE的小分子抑制剂可能具有治疗多种疾病状态的前景。本发明提供了低分子量、非肽类的基质金属蛋白酶（MMPs）和肿瘤坏死因子-α转化酶（TACE）的抑制剂，用于治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染。本发明中的化合物由以下公式表示： 其中R1、R2、R3和R4在本说明书中有所描述。

  公开号：

  US06342508B1

文献信息

• [EN] N-HYDROXY-2-(ALKYL, ARYL, OR HETEROARYL SULFANYL, SULFINYL OR SULFONYL)-3-SUBSTITUTED ALKYL, ARYL OR HETEROARYLAMIDES AS MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] N-HYDROXY-2-(ALKYL,ARYL OU HETEROARYL SULFANYL, SULFINYL OU SULFONYL)-ALKYL, ARYL OU HETEROARYLAMIDES SUBSTITUES EN POSITION 3, UTILISES COMME INHIBITEURS DES METALLOPROTEINASE MATRICIELLE
  申请人：AMERICAN CYANAMID COMPANY

  公开号：WO1998038163A1

  公开（公告）日：1998-09-03

  (EN) Matrix metalloproteinases (MMPs) are a group of enzymes that have been implicated in the pathological destruction of connective tissue and basement membranes. These zinc containing endopeptidases consist of several subsets of enzymes including collagenases, stromelysins and gelatinases. TNF-$g(a) converting enzymes (TACE), a pro-inflammatory cytokine, catalyze the formation of TNF-$g(a) from membrane-bound TNF-$g(a) precursor protein. It is expected that small molecule inhibitors of MMPs and TACE therefore have the potential for treating a variety of disease states. The present invention provides low molecular weight, non-peptide inhibitors of matrix metalloproteinases (MMPs) and TNF-$g(a) converting enzyme (TACE) for the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection. The compounds of this invention are represented by formula (I), where R1, R2, R3 and R4 are described herein.(FR) Les métalloprotéinases matricielles (MMP) sont un groupe d'enzymes ayant été impliquées dans la destruction pathologique de la membrane basale et du tissu conjonctif. Ces endopeptidases contenant du zinc consistent en plusieurs sous-ensembles d'enzymes comprenant des collagénases, des stromélysines et des gélatinases. L'enzyme de conversion de TNF-$g(a) (TACE), une cytokine pro-inflammatoire, catalyse la formation de TNF-$g(a) à partir de la protéine précurseur de TNF-$g(a) liée à la membrane. On suppose que les inhibiteurs à petites molécules de MMP et TACE ont donc la capacité de traiter plusieurs états pathologiques. L'invention se rapporte à des inhibiteurs de non peptides, à faible poids moléculaire, des métalloprotéinases matricielles (MMP) et à l'enzyme de conversion TNF-$g(a) (TACE) pour le traitement de l'arthrite, de métastases tumorales, de l'ulcération de tissu, de cicatrisation anormale, de la parodontopathie, les maladies osseuses, de diabètes (résistance à l'insuline) et de l'infection au VIH. Les composés de l'invention sont représentés par la formule (I), R1, R2, R3 et R4 étant décrits.

  基质金属蛋白酶（MMP）是一组酶，已被认为参与了结缔组织和基底膜的病理性破坏。这些含锌的内切酶由几个亚组成，包括胶原酶、基质金属蛋白酶和明胶酶。TNF-$g(a)转化酶（TACE）是一种促炎细胞因子，可催化膜结合型TNF-$g(a)前体蛋白形成TNF-$g(a)。因此，MMP和TACE的小分子抑制剂有望治疗多种疾病。本发明提供了用于治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染的基质金属蛋白酶（MMP）和TNF-$g(a)转化酶（TACE）的低分子量非肽抑制剂。本发明的化合物由公式（I）表示，其中R1、R2、R3和R4如本文所述。
• N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl, or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
  申请人：American Cyanamid Company

  公开号：US20020188120A1

  公开（公告）日：2002-12-12

  Matrix metalloproteinases (MMPs) are a group of enzymes that have been implicated in the pathological destruction of connective tissue and basement membranes. These zinc containing endopeptidases consist of several subsets of enzymes including collagenases, stromelysins and gelatinases. TNF-&agr; converting enzyme (TACE), a pro-inflammatory cytokine, catalyzes the formation of TNF-&agr; from membrane bound TNF-&agr; precursor protein. It is expected that small molecule inhibitors of MMPs and TACE therefore have the potential for treating a variety of disease states. The present invention provides low molecular weight, non-peptide inhibitors of matrix metalloproteinases (MMPs) and TNF-&agr; converting enzyme (TACE) for the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection having the formula 1 wherein R 2 and R 3 form a heterocyclic ring and A is S, S(O), or S(O)2, and R 1 and R 4 are defined herein.

  基质金属蛋白酶（MMPs）是一组酶，已被认为与结缔组织和基底膜的病理性破坏有关。这些含锌内切酶包括几个酶亚组，包括胶原酶、基质金属蛋白酶和明胶酶。TNF-α转化酶（TACE）是一种促炎细胞因子，催化膜结合的TNF-α前体蛋白形成TNF-α。因此，MMPs和TACE的小分子抑制剂有潜力用于治疗多种疾病状态。本发明提供了基质金属蛋白酶（MMPs）和TNF-α转化酶（TACE）的低分子量、非肽抑制剂，用于治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染，其化学式为1，其中R2和R3形成杂环环，A为S、S（O）或S（O）2，R1和R4如本文所定义。
• N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
  申请人：American Cyanamid Company

  公开号：US20020006922A1

  公开（公告）日：2002-01-17

  Matrix metalloproteinases (MMPs) are a group of enzymes that have been implicated in the pathological destruction of connective tissue and basement membranes. These zinc containing endopeptidases consist of several subsets of enzymes including collagenases, stromelysins and gelatinases. TNF converting enzyme (TACE), a pro-inflammatory cytokine, catalyzes the formation of TNF-&agr; from membrane bound TNF-&agr; precursor protein. It is expected that small molecule inhibitors of MMPs and TACE therefore have the potential for treating a variety of disease states. The present invention provides low molecular weight, non-peptide inhibitors of matrix metalloproteinases (is) and TNF-&agr; converting enzyme (TACE) for the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection having the formula 1 wherein R 2 and R 3 form a heterocyclic ring and A is S, S(O), or S(O)2, and R 1 and R 4 are defined herein.

  基质金属蛋白酶（MMPs）是一组酶，已被认为参与了结缔组织和基底膜的病理性破坏。这些含锌内切肽酶包括胶原酶、基质金属蛋白酶和明胶酶等几个亚组。TNF转化酶（TACE）是一种促炎细胞因子，催化膜结合型TNF-α前体蛋白形成TNF-α。预计基质金属蛋白酶和TACE的小分子抑制剂具有治疗多种疾病的潜力。本发明提供了用于治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染的基质金属蛋白酶（is）和TNF-α转化酶（TACE）的低分子量、非肽抑制剂，其化学式为1，其中R2和R3形成杂环环，A为S、S（O）或S（O）2，R1和R4如本文所定义。
• N-HYDROXY-2-(ALKYL, ARYL, OR HETEROARYL SULFANYL, SULFINYL OR SULFONYL)-3-SUBSTITUTED ALKYL, ARYL OR HETEROARYLAMIDES AS MATRIX METALLOPROTEINASE INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP0970046B1

  公开（公告）日：2003-12-10
• N-HYDROXY-2-(ALKYL, ARYL OR HETEROARYL SULFANYL, SULFINYL OR SULFONYL)-3-SUBSTITUTED ALKYL, ARYL OR HETEROARYLAMIDES AS MATRIX METALLOPROTEINASE INHIBITORS
  申请人：American Cyanamid Company

  公开号：EP0973512A1

  公开（公告）日：2000-01-26